8-K

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION

Washington, DC 20549

FORM 8-K

Current Report
Pursuant to Section 13 OR 15(d) of the Securities Exchange Act of 1934

Date of Report (Date of earliest event reported): April 29, 2009

ASPEN INSURANCE HOLDINGS LIMITED

(Exact name of registrant as specified in its charter)

Bermuda
(State or other jurisdiction
of incorporation) 001-31909
(Commission
File Number) Not Applicable
(I.R.S. Employer
Identification No.)

Maxwell Roberts Building
1 Church Street
Hamilton HM 11
Bermuda
(Address of principal executive offices)
(Zip Code)

Registrant’s telephone number, including area code: (441) 295-8201

Not Applicable
(Former name or former address, if changed since last report)

     Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:

o     Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

o     Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

o     Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

o     Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

TABLE OF CONTENTS

	Item 2.02 Results of Operations and Financial Condition
	Item 7.01 Regulation FD Disclosure
	Item 9.01- Financial Statements and Exhibits
SIGNATURES
Exhibit 99.1
Exhibit 99.2
Exhibit 99.3

Section 2 — Financial Information

Item 2.02 Results of Operations and Financial Condition

     On April 29, 2009, Aspen Insurance Holdings Limited issued a press release announcing results for the quarter ended March 31, 2009, which has been attached as Exhibit 99.1. In addition, a copy of the Aspen Insurance Holdings Limited Earnings Release Supplement for the quarter ended March 31, 2009 is attached hereto as Exhibit 99.2.

Section 7 — Regulation FD

Item 7.01 Regulation FD Disclosure

     On April 29, 2009, Aspen Insurance Holdings Limited issued a press release announcing results for the quarter ended March 31, 2009, which has been attached as Exhibit 99.1. In addition, a copy of the Aspen Insurance Holdings Limited Earnings Release Supplement for the quarter ended March 31, 2009 is attached hereto as Exhibit 99.2.

     Also, attached as Exhibit 99.3, is a slide presentation to be used for reference during the earnings call to be held on April 30, 2009.

Section 9. Financial Statements and Exhibits

Item 9.01 — Financial Statements and Exhibits

(d) The following exhibits are furnished under Items 7.01 and 2.02 as part of this report:

99.1	Press Release of the Registrant, dated April 29, 2009.
99.2	Earnings Release Supplement for the quarter ended March 31, 2009.
99.3	First Quarter 2009 Earnings Conference Call Slide Presentation, to be held on April 30, 2009.

     The information furnished under Item 7.01 “Regulation FD Disclosure” and Item 2.02 “Results of Operations and Financial Condition” shall not be deemed “filed” for purpose of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as shall be expressly set forth by specific reference in such a filing.

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SIGNATURES

     Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

	ASPEN INSURANCE HOLDINGS LIMITED                       (Registrant)
Dated: April 29, 2009	By:	/s/ Richard Houghton
		Name:	Richard Houghton
		Title:	Chief Financial Officer

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EX-99.1

Exhibit 99.1

ASPEN INSURANCE HOLDINGS REPORTS RESULTS FOR
FIRST QUARTER 2009

▪ Diluted book value per share of $29.12, up 2.2% over the first quarter of 2008 and 3.6% over the fourth quarter of 2008.

▪ First quarter net income of $91.4 million, up 12.6% over the same quarter last year.

▪ First quarter net investment income of $59.2 million, up 51.4% over the same quarter last year.

▪ Operating earnings per share of $1.18 for the quarter, up 49.4% over the first quarter of 2008.

▪ Annualized operating return on equity of 17.6% for the quarter.

HAMILTON, BERMUDA, April 29, 2009 — Aspen Insurance Holdings Limited (NYSE: AHL) today reported a net profit after tax for the first quarter of 2009 of $91.4 million and operating earnings of $1.18 per diluted ordinary share. This compares to a net profit after tax of $81.2 million, and operating earnings of $0.79 per diluted share for the first quarter last year.

Book value per share on a diluted basis of $29.12 increased by $0.64 when compared to March 31, 2008 and by $1.02 since the end of December 2008, mainly as a result of $72.2 million of retained income generated during the first quarter of 2009.

On March 31, 2009, Aspen repurchased $66.8 million in nominal value of its 7.401% $25 perpetual preference shares for $34.1 million and issued $25.1 million of ordinary shares, in accordance with the replacement capital covenant which formed part of the initial preference share transaction. This repurchase increased diluted book value per share and diluted net income per share for the first quarter of 2009 by $0.37 and $0.38, respectively.

First Quarter 2009 Financial Highlights

($ in millions, except per share amounts and percentages)

(Unaudited)

	Q1 2009			Q1 2008			Change
Gross written premium	$	636.8		$	596.2			6.8	%
Net earned premium	$	447.3		$	391.6			14.2	%
Net investment income	$	59.2		$	39.1			51.4	%
Net income after tax	$	91.4		$	81.2			12.6	%
Diluted net income per share	$	1.39		$	0.85			63.5	%
Diluted operating earnings per share	$	1.18		$	0.79			49.4	%
Net income annualized return on equity		14.8	%		12.8	%
Annualized operating return on equity		17.6	%		12.0	%
Combined ratio		84.5	%		85.4	%
Diluted book value per share	$	29.12		$	28.48			2.2	%

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Chris O’Kane, Chief Executive Officer said, “We had a good first quarter  with continued growth in book value per share of almost 4% since the end of 2008 and positive underwriting contributions from each of our four business segments. Aspen is well positioned to benefit from the improving rate environment in a number of our core lines of business. Our balance sheet remains strong and we will continue to focus on active deployment of our capital to those segments where we see most opportunity consistent with our diversified business model. ”

First Quarter 2009 Operating Highlights

▪ Combined ratio of 84.5% for the quarter compared with 85.4% for the first quarter of 2008.

▪ Expense ratio of 28.4% for the quarter, down from 32.5% over the same quarter last year.

▪ Repurchased perpetual preference shares with a nominal value of $66.8 million for $34.1 million.

▪ Cash flows from operating activities of $203.2 million compared with $163.5 million in the first quarter of 2008.

▪ Reserve release of $9.8 million for the quarter compared with $39.5 million in the first quarter of 2008.

Business Segment Highlights

A summary of the operating highlights for each of Aspen’s four business segments is presented below.

Property Reinsurance

Our property reinsurance segment recorded a combined ratio of 57.6% for the quarter compared with 63.4% for the same period in 2008. The main driver for the improvement in the combined ratio is the increase in gross earned premiums. Gross written premiums for the first quarter of 2009 were $220.5 million compared to $184.2 million in the equivalent period in 2008. The increase in gross written premiums is attributable to improving market conditions and favorable prior year premium development.

Casualty Reinsurance

The casualty reinsurance segment combined ratio improved to 94.1% for the quarter from 94.9% in the first quarter of 2008. The combined ratio in the current quarter has benefited from favorable exchange rate movements coupled with reserve releases of $3.1 million whereas the first quarter of 2008 benefited from prior year releases of $14.3 million. Gross written premium of $186.8 million is up slightly from $182.1 million in the first quarter of 2008.

International Insurance

The international insurance segment reported a combined ratio for the first quarter of 99.2% versus 95.5% in the first quarter of 2008. This segment had mixed loss experience for both prior year claims and current year losses with limited adverse prior year deterioration in respect of those lines exposed to the global financial crisis. Gross written premiums in the quarter of $194.7 million are down slightly from $199.3 million in the first quarter of 2008.

U.S. Insurance

The combined ratio in the first quarter for the U.S. insurance segment has improved to 88.7% compared with 103.6% in the first quarter of 2008 due to favorable loss experience in the current quarter and an increase in earned premium. Gross written premium for the first quarter of 2009 was $34.8 million, an increase of 13.7% when compared to the first quarter of 2008. 

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Investment Performance

Net investment income for the quarter was $59.2 million compared with $39.1 million in the first quarter of 2008 due primarily to the $4.0 million contribution from our funds of hedge funds investments, compared to $16.9 million of losses from these investments in the first quarter of 2008. Annualized total investment return for the quarter was 3.4%.

The book yield on the fixed income portfolio was 4.42% at the end of the first quarter of 2009, down from 4.64% at December 31, 2008. Unrealized gains on the fixed income portfolio at the end of the first quarter of 2009 were $70.7 million, an increase of $3.3 million from the end of the fourth quarter of 2008. Other-than-temporary impairment charges were $15.2 million for the first quarter of 2009.

The portfolio consists of high quality diversified assets, with 30.9% of fixed maturity assets invested in U.S. Government and other foreign government bonds and 22.7% invested in agency-issued mortgage-backed securities. The average credit quality of the portfolio is AA+ with an average duration of 2.9 years.

Outlook for 2009

The Company anticipates total gross written premium of $2 billion +/- 5%, premium ceded of 10% to 12% of gross earned premium, a combined ratio in the range of 88% to 94%, a tax rate of 13% to 16% and a cat-load of $140 million for the remainder of the year, assuming normal loss experience.

Earnings conference call

Aspen will hold a conference call to discuss its financial results on Thursday, April 30, 2009 at 8:30 a.m. (Eastern Time).

CONFERENCE CALL PARTICIPATION DETAILS – April 30, 2009 at 8:30 a.m. (EST)

Participant Dial-In Numbers:	+1 (888) 459-5609 (US Toll Free)
	+1 (404) 665-9920 (International)
Conference ID:	91944234

Please call to register at least 10 minutes before the conference call begins.

The conference call will be webcast live in the ‘presentations’ section of the Investor Relations page of Aspen’s website, which is located at www.aspen.bm. The earnings press release and a detailed financial supplement will be posted to the website, as well as a brief slide presentation which may be used for reference during the earnings call.

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REPLAY DETAILS

A replay of the call will be available for 14 days via telephone and Internet starting two hours following the end of the live call.

Replay Access:	+1 (800) 642-1687 (US Toll Free)
	+1 (706) 645-9291 (International)
	www.aspen.bm
Replay ID:	91944234

Investor Contact:
Aspen Insurance Holdings Limited
Noah Fields, Head of Investor Relations	T: +1 441-297-9382
European Press Contact:
Citigate Dewe Rogerson
Justin Griffiths/Sarah Gestetner	T: +44 (0) 20 7282 2920
North American Press Contact:
Abernathy MacGregor
Carina Davidson/Allyson Morris	T: +1 212-371-5999

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Aspen Insurance Holdings Limited
Summary Consolidated Balance Sheet
($ in millions, except per share data)
(Unaudited)

	As at March 31,		As at December 31,
(in US$ millions)	2009		2008
ASSETS
Total investments	$	5,149.3	$	4,944.9
Cash and cash equivalents		913.2		809.1
Reinsurance recoverable		436.7		329.6
Premiums receivable		793.6		677.5
Other assets		347.0		527.7
Total assets	$	7,639.8	$	7,288.8
LIABILITIES
Losses and loss adjustment expenses	$	3,096.2	$	3,070.3
Unearned premiums		963.8		810.7
Other payables		497.8		379.2
Long-term debt		249.6		249.5
Total liabilities	$	4,807.4	$	4,509.7
SHAREHOLDERS’ EQUITY
Total shareholders’ equity		2,832.4		2,779.1
Total liabilities and shareholders’ equity	$	7,639.8	$	7,288.8
Tangible book value per share	$	29.85	$	28.85
Diluted book value per share (treasury stock method)	$	29.12	$	28.10

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Aspen Insurance Holdings Limited
Summary Consolidated Statements of Income
($ in millions, except share, per share data and ratios)
(Unaudited)

	Three Months Ended			Three Months Ended
(in US$ millions)	March 31, 2009			March 31, 2008
UNDERWRITING REVENUES
Gross written premiums	$	636.8		$	596.2
Premiums ceded		(130.2	)		(76.6	)
Net written premiums		506.6			519.6
Change in unearned premiums		(59.3	)		(128.0	)
Net earned premiums	$	447.3		$	391.6
UNDERWRITING EXPENSES
Losses and loss expenses		250.8			207.2
Acquisition expenses		78.6			76.4
General and administrative expenses		48.5			50.8
Total underwriting expenses		377.9			334.4
Underwriting income	$	69.4		$	57.2
OTHER OPERATING REVENUE
Net investment income		59.2			39.1
Interest expense		(3.9	)		(3.9	)
Total other operating revenue	$	55.3		$	35.2
Other income (expense)		(2.7	)		(2.2	)
OPERATING INCOME BEFORE TAX		122.0			90.2
OTHER
Net realized and unrealized exchange (losses) gains		(2.3	)		4.3
Net realized investment (losses) gains		(12.2	)		1.0
INCOME BEFORE TAX		107.5			95.5
Income taxes expense		(16.1	)		(14.3	)
NET INCOME AFTER TAX		91.4			81.2
Dividends paid on ordinary shares		(12.3	)		(12.9	)
Dividend paid on preference shares		(6.9	)		(6.9	)
Retained income	$	72.2		$	61.4
Components of net income (after tax)
Operating income		105.7			76.0
Net realized and unrealized exchange (losses) gains after tax		(2.3	)		4.3
Net realized investment (losses) gains after tax		(12.0	)		0.9
NET INCOME AFTER TAX	$	91.4		$	81.2
Loss ratio		56.1	%		52.9	%
Policy acquisition expense ratio		17.6	%		19.5	%
General and administrative expense ratio		10.8	%		13.0	%
Expense ratio		28.4	%		32.5	%
Combined ratio		84.5	%		85.4	%

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Aspen Insurance Holdings Limited
Summary Consolidated Financial Data
($ in millions, except share, per share data and ratios)
(Unaudited)

	Three Months Ended		Three Months Ended
(in US$ except for number of shares)	March 31, 2009		March 31, 2008
Basic earnings per ordinary share
Net income adjusted for preference share dividend and cancellation of preference shares	$	1.42	$	0.87
Operating income adjusted for preference dividend	$	1.21	$	0.81
Diluted earnings per ordinary share
Net income adjusted for preference share dividend and cancellation of preference shares	$	1.39	$	0.85
Operating income adjusted for preference dividend	$	1.18	$	0.79
Weighted average number of ordinary shares outstanding (in millions)		81.535		85.511
Weighted average number of ordinary shares outstanding and dilutive potential ordinary shares (in millions)		83.572		87.957

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Aspen Insurance Holdings Limited
Summary Consolidated Segment Information
($ in millions except ratios)
(Unaudited)

	Three Months			Three Months
	Ended March 31,			Ended March 31,
	2009			2008
Gross written premiums
Property Reinsurance	$	220.5		$	184.2
Casualty Reinsurance		186.8			182.1
International Insurance		194.7			199.3
U.S. Insurance		34.8			30.6
Total	$	636.8		$	596.2
Premiums ceded
Property Reinsurance	$	38.4		$	8.8
Casualty Reinsurance		1.0			2.1
International Insurance		69.9			57.3
U.S. Insurance		20.9			8.4
Total	$	130.2		$	76.6
Net written premiums
Property Reinsurance	$	182.1		$	175.4
Casualty Reinsurance		185.8			180.0
International Insurance		124.8			142.0
U.S. Insurance		13.9			22.2
Total	$	506.6		$	519.6
Net earned premiums
Property Reinsurance	$	139.1		$	127.0
Casualty Reinsurance		109.5			94.7
International Insurance		175.0			150.2
U.S. Insurance		23.7			19.7
Total	$	447.3		$	391.6
Underwriting profit
Property Reinsurance	$	58.9		$	46.5
Casualty Reinsurance		6.4			4.8
International Insurance		1.4			6.6
U.S. Insurance		2.7			(0.7	)
Total	$	69.4		$	57.2
Combined ratio
Property Reinsurance		57.6	%		63.4	%
Casualty Reinsurance		94.1	%		94.9	%
International Insurance		99.2	%		95.5	%
U.S. Insurance		88.7	%		103.6	%
Total		84.5	%		85.4	%

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About Aspen Insurance Holdings Limited

Aspen provides reinsurance and insurance coverage to clients in various domestic and global markets through wholly-owned subsidiaries and offices in Bermuda, France, Ireland, Singapore, the United States, the United Kingdom, and Switzerland. For the three months ended March 31, 2009, Aspen reported gross written premiums of $636.8 million, net income of $94.1 million and total assets of $7.6 billion. Its operating subsidiaries have been assigned a rating of “A” (“Strong”) by Standard & Poor’s, an “A” (“Excellent”) by A.M. Best and an “A2” (“Good”) by Moody’s Investors Service. For more information about Aspen, please visit www.aspen.bm.

Application of the Safe Harbor of the Private Securities Litigation Reform Act of 1995:

This press release contains, and Aspen’s earnings conference call will contain, written or oral “forward-looking statements” within the meaning of the U.S. federal securities laws. These statements are made pursuant to the safe harbor provisions of the Private Securities Litigation Reform Act of 1995. Forward-looking statements include all statements that do not relate solely to historical or current facts, and can be identified by the use of words such as “expect,” “intend,” “plan,” “believe,” “project,” “anticipate,” “seek,” “will,” “estimate,” “may,” “continue,” “guidance,” and similar expressions of a future or forward-looking nature.

All forward-looking statements address matters that involve risks and uncertainties. Accordingly, there are or will be important factors that could cause actual results to differ materially from those indicated in these statements. Aspen believes these factors include, but are not limited to: the continuing and uncertain impact of the current depressed credit environment, the banking crises and economic recessions in many of the countries in which we operate and of the measures being taken by governments to counter these issues; the risk of a material decline in the value or liquidity of all or parts of our investment portfolio; changes in insurance and reinsurance market conditions that could adversely impact execution of the business plan; changes in our ability to exercise capital management or strategic initiatives or to arrange banking facilities as a result of prevailing market changes or changes in our financial position; our ability to execute our business plan to enter new markets, introduce new products and develop new distribution channels, including their integration into our existing operations; increased counterparty risk due to the impairment of financial institutions; changes in the total industry losses, or our share of total industry losses, resulting from past events such as Hurricanes Ike and Gustav and, with respect to such events, our reliance on loss reports received from cedants and loss adjustors, our reliance on industry loss estimates and those generated by modelling techniques, changes in rulings on flood damage or other exclusions as a result of prevailing lawsuits and case law, any changes in our reinsurers’ credit quality and the amount and timing of reinsurance recoverables; the impact of acts of terrorism and related legislation and acts of war; the possibility of greater frequency or severity of claims and loss activity, including as a result of natural or man-made catastrophic events, than our underwriting, reserving, reinsurance purchasing or investment practices have anticipated; evolving interpretive issues with respect to coverage after major loss events; the level of inflation in repair costs due to limited availability of labor and materials after catastrophes; the effectiveness of our loss limitation methods; changes in the availability, cost or quality of reinsurance or retrocessional coverage; the reliability of, and changes in assumptions to, catastrophe pricing, accumulation and estimated loss models; loss of key personnel; a decline in our operating subsidiaries’ ratings with Standard & Poor’s (“S&P”), A.M. Best or Moody’s Investors Service (“Moody’s”); changes in general economic conditions, including inflation, foreign currency exchange rates, interest rates and other factors that could affect our investment portfolio; the number and type of insurance and reinsurance contracts that we wrote at the January 1^st and other renewal periods in 2009 and the premium rates available at the time of such renewals within our targeted business lines; increased competition on the basis of pricing, capacity, coverage terms or other factors and the related demand and supply dynamics as contracts come up for renewal; decreased demand for our insurance or reinsurance products and cyclical changes in the insurance and reinsurance sectors; changes in government regulations or tax laws in jurisdictions where we conduct business; and Aspen or its Bermudian subsidiary becoming subject to income taxes in the United States or the United Kingdom; and the effect on insurance markets, business practices and relationships of ongoing litigation, investigations and regulatory activity by insurance regulators and prosecutors. For a more detailed description of these uncertainties and other factors, please see the “Risk Factors” section in Aspen’s Annual Reports on Form 10-K as filed with the U.S. Securities and Exchange Commission on February 26, 2009. Aspen undertakes no obligation to publicly update or revise any forward-looking statements, whether as a result of new information, future events or otherwise. Readers are cautioned not to place undue reliance on these forward-looking statements, which speak only as of the dates on which they are made.

In addition, any estimates relating to loss events involve the exercise of considerable judgment and reflect a combination of ground-up evaluations, information available to date from brokers and cedants, market intelligence, initial tentative loss reports and other sources. Due to the complexity of factors contributing to the losses and the preliminary nature of the information used to prepare these estimates, there can be no assurance that Aspen’s ultimate losses will remain within the stated amount.

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Non-GAAP Financial Measures

In presenting Aspen’s results, management has included and discussed certain “non-GAAP financial measures” as such term is defined in Regulation G. Management believes that these non-GAAP measures, which may be defined differently by other companies, better explain Aspen’s results of operations in a manner that allows for a more complete understanding of the underlying trends in Aspen’s business. However, these measures should not be viewed as a substitute for those determined in accordance with GAAP. The reconciliation of such non-GAAP financial measures to their respective most directly comparable GAAP financial measures in accordance with Regulation G is included in the financial supplement, which can be obtained from the Investor Relations section of Aspen’s website at www.aspen.bm.

(1) Annualized Operating Return on Average Equity (“Operating ROE”) is a non-GAAP financial measure. Annualized Operating Return on Average Equity 1) is calculated using operating income, as defined below and 2) excludes from average equity, the average after-tax unrealized appreciation or depreciation on investments and the average after-tax unrealized foreign exchange gains or losses and the aggregate value of the liquidation preferences of our preference shares. Unrealized appreciation (depreciation) on investments is primarily the result of interest rate movements and the resultant impact on fixed income securities, and unrealized appreciation (depreciation) on foreign exchange is the result of exchange rate movements between the U.S. dollar and the British pound. Such appreciation (depreciation) is not related to management actions or operational performance (nor is it likely to be realized). Therefore, Aspen believes that excluding these unrealized appreciations (depreciations) provides a more consistent and useful measurement of operating performance, which supplements GAAP information. Average equity is calculated as the arithmetic average on a monthly basis for the stated periods.

Aspen presents Operating ROE as a measure that is commonly recognized as a standard of performance by investors, analysts, rating agencies and other users of its financial information.

See page 27 of Aspen’s financial supplement for a reconciliation of operating income to net income and page 8 for a reconciliation of average equity.

(2) Annualized Operating Return on Average Equity excluding gains or losses from funds of hedge funds (“Adjusted Operating ROE”) is a non-GAAP financial measure. Annualized Operating Return on Average Equity excluding gains or losses from funds of hedge funds 1) is calculated using adjusted operating income, as defined below and 2) excludes from average equity, the average after-tax unrealized appreciation or depreciation on investments and the average after-tax unrealized foreign exchange gains or losses and the aggregate value of the liquidation preferences of our preference shares. Unrealized appreciation (depreciation) on investments is primarily the result of interest rate movements and the resultant impact on fixed income securities, and unrealized appreciation (depreciation) on foreign exchange is the result of exchange rate movements between the U.S. dollar and the British pound. Such appreciation (depreciation) is not related to management actions or operational performance (nor is it likely to be realized). Therefore, Aspen believes that excluding these unrealized appreciations (depreciations) provides a more consistent and useful measurement of operating performance, which supplements GAAP information. Average equity is calculated as the arithmetic average on a monthly basis for the stated periods.

Aspen presents Adjusted Operating ROE as a measure that is commonly recognized as a standard of performance by investors, analysts, rating agencies and other users of its financial information.

See page 29 of Aspen’s financial supplement for a reconciliation of adjusted operating income to net income and page 8 for a reconciliation of average equity.

(3) Operating income is a non-GAAP financial measure. Operating income is an internal performance measure used by Aspen in the management of its operations and represents after-tax operational results excluding, as applicable, after-tax net realized capital gains or losses and after-tax net foreign exchange gains or losses.

Aspen excludes after-tax net realized capital gains or losses and after-tax net foreign exchange gains or losses from its calculation of operating income because the amount of these gains or losses is heavily influenced by, and fluctuates in part, according to the availability of market opportunities. Aspen believes these amounts are largely independent of its business and underwriting process and including them distorts the analysis of trends in its operations. In addition to presenting net income determined in accordance with GAAP, Aspen believes that showing operating income enables investors, analysts, rating agencies and other users of its financial information to more easily analyze Aspen’s results of operations in a manner similar to how management analyzes Aspen’s underlying business performance. Operating income should not be viewed as a substitute for GAAP net income. Please see above and page 27 of Aspen’s financial supplement for a reconciliation of operating income to net income. Aspen’s financial supplement can be obtained from the Investor Relations section of Aspen’s website at www.aspen.bm.

(4) Adjusted Operating income is a non-GAAP financial measure. Adjusted operating income is an internal performance measure used by Aspen in the management of its operations and represents after-tax operational results excluding, as applicable, after-tax net realized capital gains or losses, after-tax net foreign exchange gains or losses and excludes after tax net gains or losses from our investments in funds of hedge funds.

Aspen excludes after-tax net realized capital gains or losses, after-tax net foreign exchange gains or losses and after tax net gains or losses from our investments in funds of hedge funds from its calculation of operating income because

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the amount of these gains or losses is heavily influenced by, and fluctuates in part, according to the availability of market opportunities. Aspen believes these amounts are largely independent of its business and underwriting process and including them distorts the analysis of trends in its operations. In addition to presenting net income determined in accordance with GAAP, Aspen believes that showing operating income enables investors, analysts, rating agencies and other users of its financial information to more easily analyze Aspen’s results of operations in a manner similar to how management analyzes Aspen’s underlying business performance. Operating income should not be viewed as a substitute for GAAP net income. Please see above and page 29 of Aspen’s financial supplement for a reconciliation of adjusted operating income to net income. Aspen’s financial supplement can be obtained from the Investor Relations section of Aspen’s website at www.aspen.bm.

(5) Diluted book value per ordinary share is a non-GAAP financial measure. Aspen has included diluted book value per ordinary share because it takes into account the effect of dilutive securities; therefore, Aspen believes it is a better measure of calculating shareholder returns than book value per share. Please see page 26 of Aspen’s financial supplement for a reconciliation of diluted book value per share to basic book value per share. Aspen’s financial supplement can be obtained from the Investor Relations section of Aspen’s website at www.aspen.bm.

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EX-99.2

Exhibit 99.2

Aspen Insurance Holdings Limited

Financial Supplement

As of March 31, 2009

This financial supplement is for information purposes only. It should be read in
conjunction with other documents filed or to be filed by Aspen Insurance
Holdings Limited with the United States Securities and Exchange Commission.

AHL: NYSE

www.aspen.bm

Investor Contact:

Aspen Insurance Holdings Limited

Noah Fields, Head of Investor Relations

T: +1 441-297-9382

email: noah.fields@aspen-re.com

Aspen Insurance Holdings Limited

Table Of Contents

	Page
Basis of Presentation		1-2
Financial Highlights		3
Consolidated Statements of Operations — Quarterly		4
Consolidated Statements of Operations — Year to Date		5
Consolidated Balance Sheets		6
Earnings Per Share and Book Value Per Share		7
Return on Average Equity		8
Consolidated Underwriting Results By Operating Segment		9
Operating Segment — Quarterly Results		10-13
Gross Written Premiums by Segment and Line of Business		14
Accident Year Loss Ratios		15
Consolidated Statements of Changes In Shareholders’ Equity		16
Consolidated Statements of Comprehensive Income		17
Consolidated Statements of Cash Flows		18
Reserves For Losses and Loss Expenses		19
Reserves By Operating Segment		20
Prior Year Reserve Releases		21
Ratings Of Reinsurers		22
Consolidated Investment Portfolio		23
Investment Analysis		24
Book Value Per Ordinary Share		25
Diluted Share Analysis		26
Operating Income Reconciliation		27
Net Income Reconciliation		28
Adjusted Operating Income Reconciliation		29

Aspen Insurance Holdings Limited

Basis of Presentation

Definitions and presentation: All financial information contained herein is unaudited except for information for the fiscal year ended December 31, 2008. Unless otherwise noted, all data is in U.S. dollars millions, except for per share, percentage and ratio information.

In presenting Aspen’s results, management has included and discussed certain “non-GAAP financial measures”, as such term is defined in Regulation G. Management believes that these non-GAAP measures, which may be defined differently by other companies, better explain Aspen’s results of operations in a manner that allows for a more complete understanding of the underlying trends in Aspen’s business. However, these measures should not be viewed as a substitute for those determined in accordance with GAAP. The reconciliation of such non-GAAP financial measures to their respective most directly comparable GAAP financial measures in accordance with Regulation G is included in this financial supplement.

Operating income (a non-GAAP financial measure): Operating income is an internal performance measure used by Aspen in the management of its operations and represents after-tax operational results excluding, as applicable, after-tax net realized capital gains or losses and after-tax net foreign exchange gains or losses.

Aspen excludes after-tax net realized capital gains or losses and after-tax net foreign exchange gains or losses from its calculation of operating income because the amount of these gains or losses is heavily influenced by, and fluctuates in part, according to the availability of market opportunities. Aspen believes these amounts are largely independent of its business and underwriting process and including them distorts the analysis of trends in its operations. In addition to presenting net income determined in accordance with GAAP, Aspen believes that showing operating income enables investors, analysts, rating agencies and other users of its financial information to more easily analyze Aspen’s results of operations in a manner similar to how management analyzes Aspen’s underlying business performance. Operating income should not be viewed as a substitute for GAAP net income. Please see page 27 for a reconciliation of operating income to net income.

Net income excluding net income or losses from investments accounted for by the equity method (a non-GAAP financial measure): This is an internal performance measure used by Aspen in the management of its operations and represents net income adjusted for preference share dividends excluding after-tax net income or losses from investments accounted for using the equity method.

Aspen excludes net income or loss from investments accounted for using the equity method from its calculation of net income because the amount of these gains or losses are largely independent of its business and underwriting process and including them distorts the analysis of trends in its operations. In addition to presenting net income determined in accordance with GAAP, Aspen believes that showing net income excluding net income or losses for other investments accounted for by the equity method enables investors, analysts, rating agencies and other users of its financial information to more easily analyze Aspen’s results of operations in a manner similar to how management analyzes Aspen’s underlying business performance. Net income excluding net income or losses for investments accounted for by the equity method should not be viewed as a substitute for GAAP net income. Please see page 28 for a reconciliation of net income excluding net income or losses for other investments accounted for by the equity method income to net income.

Adjusted Operating income (a non-GAAP financial measure): Adjusted operating income is an internal performance measure used by Aspen in the management of its operations and represents after-tax operational results excluding, as applicable, after-tax net realized capital gains or losses, after-tax net foreign exchange gains or losses and after-tax gains or losses from our investments in funds of hedge funds.

Aspen excludes after-tax net realized capital gains or losses, after-tax net foreign exchange gains or losses and after-tax gains or losses from our investments in funds of hedge funds from its calculation of adjusted operating income because the amount of these gains or losses is heavily influenced by, and fluctuates in part, according to the availability of market opportunities. Aspen believes these amounts are largely independent of its business and underwriting process and including them distorts the analysis of trends in its operations. In addition to presenting net income determined in accordance with GAAP, Aspen believes that showing adjusted operating income enables investors, analysts, rating agencies and other users of its financial information to more easily analyze Aspen’s results of operations in a manner similar to how management analyzes Aspen’s underlying business performance. Adjusted operating income should not be viewed as a substitute for GAAP net income. Please see page 29 for a reconciliation of adjusted operating income to net income.

Annualized Operating Return on Average Equity (“Operating ROE”) (a non-GAAP financial measure: Annualized Operating Return on Average Equity 1) is calculated using operating income, as defined above and 2) excludes from average equity, the average after-tax unrealized appreciation or depreciation on investments and the average after-tax unrealized foreign exchange gains or losses and the aggregate value of the liquidation preferences of our preference shares. Unrealized appreciation (depreciation) on investments is primarily the result of interest rate movements and the resultant impact on fixed income securities, and unrealized appreciation (depreciation) on foreign exchange is the result of exchange rate movements between the U.S. dollar and the British pound. Such appreciation (depreciation) is not related to management actions or operational performance (nor is it likely to be realized). Therefore, Aspen believes that excluding these unrealized appreciations (depreciations) provides a more consistent and useful measurement of operating performance, which supplements GAAP information. Average equity is calculated as the arithmetic average on a monthly basis for the stated periods.

Aspen presents Operating ROE as a measure that is commonly recognized as a standard of performance by investors, analysts, rating agencies and other users of its financial information. See page 27 for a reconciliation of operating income to net income and page 8 for a reconciliation of average equity to closing shareholders’ equity.

1

Aspen Insurance Holdings Limited

Basis of Presentation

Annualized Operating Return on Average Equity excluding gains or losses from funds of hedge funds (“Adjusted Operating ROE”) (a non-GAAP financial measure: Annualized Operating Return on Average Equity excluding gains or losses from funds of hedge funds 1) is calculated using operating income, as defined below and 2) excludes from average equity, the average after-tax unrealized appreciation or depreciation on investments and the average after-tax unrealized foreign exchange gains or losses and the aggregate value of the liquidation preferences of our preference shares. Unrealized appreciation (depreciation) on investments is primarily the result of interest rate movements and the resultant impact on fixed income securities, and unrealized appreciation (depreciation) on foreign exchange is the result of exchange rate movements between the U.S. dollar and the British pound. Such appreciation (depreciation) is not related to management actions or operational performance (nor is it likely to be realized). Therefore, Aspen believes that excluding these unrealized appreciations (depreciations) provides a more consistent and useful measurement of operating performance, which supplements GAAP information. Average equity is calculated as the arithmetic average on a monthly basis for the stated periods.

See page 29 for a reconciliation of adjusted operating income to net income and page 8 for a reconciliation of average equity.

Diluted book value per ordinary share (a non-GAAP financial measure): Aspen has included diluted book value per ordinary share because it takes into account the effect of dilutive securities; therefore, Aspen believes it is a better measure of calculating shareholder returns than book value per share. Please see page 25 for a reconciliation of diluted book value per share to basic book value per share.

Underwriting ratios (GAAP financial measures): Aspen, along with others in the industry, uses underwriting ratios as measures of performance. The loss ratio is the ratio of net claims and claims adjustment expenses to net premiums earned. The acquisition expense ratio is the ratio of underwriting expenses (commissions; premium taxes, licenses and fees; as well as other underwriting expenses) to net premiums earned. The general and administrative expense ratio is the ratio of general and administrative expenses to net premiums earned. The combined ratio is the sum of the loss ratio, the acquisition expense ratio and the general and administrative expense ratio. These ratios are relative measurements that describe for every $100 of net premiums earned or written, the cost of losses and expenses, respectively. The combined ratio presents the total cost per $100 of earned premium. A combined ratio below 100% demonstrates underwriting profit; a combined ratio above 100% demonstrates underwriting loss.

GAAP combined ratios differ from U.S. statutory combined ratios primarily due to the deferral of certain third party acquisition expenses for GAAP reporting purposes and the use of net premiums earned rather than net premiums written in the denominator when calculating the acquisition expense and the general and administrative expense ratios.

Accident Year Loss Ratios (a non-GAAP financial measure): In addition to the underwriting ratios described above, management also uses accident year loss ratios to evaluate current underwriting performance. The accident year loss ratio excludes the effect of prior years’ premium adjustments and reserve developments. This ratio focuses on the relationship between current premiums earned and losses incurred related to the current year. Please see page 15 for a reconciliation of accident year loss ratios to underwriting ratios calculated in accordance with U.S. GAAP.

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Aspen Insurance Holdings Limited
Financial Highlights

	Three Months Ended March 31,
(in US$ millions except for percentages, share and per share amounts)	2009			2008			Change
Gross written premium	$	636.8		$	596.2			6.8	%
Net written premium	$	506.6		$	519.6			(2.5	%	)
Net earned premium	$	447.3		$	391.6			14.2	%
Net income after tax	$	91.4		$	81.2			12.6	%
Operating income after tax	$	105.7		$	76.0			39.1	%
Investment income	$	59.2		$	39.1			51.4	%
Underwriting income	$	69.4		$	57.2			21.3	%
Earnings Per Share and Book Value Per Share
Basic earnings per ordinary share
Net income adjusted for preference share dividend and cancellation of preference shares	$	1.42		$	0.87			63.2	%
Operating income adjusted for preference share dividend	$	1.21		$	0.81			49.4	%
Diluted earnings per ordinary share
Net income adjusted for preference share dividend and cancellation of preference shares	$	1.39		$	0.85			63.5	%
Operating income adjusted for preference share dividend	$	1.18		$	0.79			49.4	%
Book value per ordinary share	$	29.85		$	29.22			2.2	%
Diluted book value per ordinary share (treasury stock method)	$	29.12		$	28.48			2.2	%
Weighted average number of ordinary shares outstanding (in millions of shares)		81.535			85.511			(4.6	%	)
Diluted weighted average number of ordinary shares outstanding (in millions of shares)		83.572			87.957			(5.0	%	)
Underwriting Ratios
Loss ratio		56.1	%		52.9	%
Policy acquisition cost ratio		17.6	%		19.5	%
General and administrative expense ratio		10.8	%		13.0	%
Expense ratio		28.4	%		32.5	%
Combined ratio		84.5	%		85.4	%
Return On Equity
Average equity (1)	$	2,270.5		$	2,318.2
Return on average equity
Net income adjusted for preference share dividend		3.7	%		3.2	%
Operating income adjusted for preference share dividend		4.4	%		3.0	%
Annualized return on average equity
Net income		14.8	%		12.8	%
Operating income		17.6	%		12.0	%

See pages 8, 25, 27, 28 and 29 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures.

1. Average equity excludes the average after-tax unrealized appreciation or depreciation on investments and average after-tax unrealized foreign exchange gains or losses.

3

Aspen Insurance Holdings Limited

Consolidated Statements Of Operations — Quarterly

(in US$ millions except for percentages)	Q1 2009			Q4 2008			Q3 2008			Q2 2008			Q1 2008			Q1 2007
UNDERWRITING REVENUES
Gross written premiums		$636.8			$435.4			$441.3			$528.8			$596.2			$636.5
Premiums ceded		(130.2	)		(29.3	)		(37.5	)		(22.8	)		(76.6	)		(81.4	)
Net written premiums		506.6			406.1			403.8			506.0			519.6			555.1
Change in unearned premiums		(59.3	)		72.5			30.4			(108.7	)		(128.0	)		(116.1	)
Net earned premiums		447.3			478.6			434.2			397.3			391.6			439.0
UNDERWRITING EXPENSES
Losses and loss expenses		250.8			310.6			413.4			188.3			207.2			225.5
Acquisition expenses		78.6			87.5			70.4			65.0			76.4			77.7
General and administrative expenses		48.5			48.6			51.6			57.1			50.8			45.3
Total underwriting expenses		377.9			446.7			535.4			310.4			334.4			348.5
Underwriting income (loss)		69.4			31.9			(101.2	)		86.9			57.2			90.5
OTHER OPERATING REVENUE
Net investment income		59.2			10.3			19.3			70.5			39.1			67.5
Interest expense		(3.9	)		(3.9	)		(3.8	)		(4.0	)		(3.9	)		(4.2	)
Total other operating revenue		55.3			6.4			15.5			66.5			35.2			63.3
Other (expense) income		(2.7	)		(0.5	)		0.6			—			(2.2	)		(7.3	)
OPERATING INCOME (LOSS) BEFORE TAX		122.0			37.8			(85.1	)		153.4			90.2			146.5
OTHER
Net realized and unrealized exchange (losses) gains		(2.3	)		(4.8	)		(2.7	)		(5.0	)		4.3			5.5
Net realized investment (losses) gains		(12.2	)		8.4			(58.1	)		0.8			1.0			(4.8	)
INCOME (LOSS) BEFORE TAX		107.5			41.4			(145.9	)		149.2			95.5			147.2
Income tax (expense) recovery		(16.1	)		(19.6	)		19.8			(22.3	)		(14.3	)		(25.3	)
NET INCOME (LOSS) AFTER TAX		91.4			21.8			(126.1	)		126.9			81.2			121.9
Dividends paid on ordinary shares		(12.3	)		(12.3	)		(12.2	)		(12.8	)		(12.9	)		(13.2	)
Dividend paid on preference shares		(6.9	)		(6.9	)		(6.9	)		(7.0	)		(6.9	)		(6.9	)
Retained income (loss)		$72.2			$2.6			$(145.2	)		$107.1			$61.4			$101.8
Components of net income (loss) after tax
Operating income (loss)		$105.7			$20.5			$(76.2	)		$131.2			$76.0			$120.6
Net realized and unrealized exchange (losses) gains after tax		(2.3	)		(4.8	)		(2.7	)		(5.0	)		4.3			5.5
Net realized investment gains (losses) after tax		(12.0	)		6.1			(47.2	)		0.7			0.9			(4.2	)
NET INCOME (LOSS) AFTER TAX		$91.4			$21.8			$(126.1	)		$126.9			$81.2			$121.9
Loss ratio		56.1%			64.9%			95.2%			47.4%			52.9%			51.4%
Policy acquisition expense ratio		17.6%			18.3%			16.2%			16.4%			19.5%			17.7%
General and administrative expense ratio		10.8%			10.2%			11.9%			14.4%			13.0%			10.3%
Expense ratio		28.4%			28.5%			28.1%			30.8%			32.5%			28.0%
Combined ratio		84.5%			93.4%			123.3%			78.2%			85.4%			79.4%
Basic earnings per share(1)		$1.42			$0.18			$(1.63	)		$1.44			$0.87			$1.31
Diluted earnings per share(1)		$1.39			$0.18			$(1.63	)		$1.39			$0.85			$1.27
Annualized return on average equity
Net income		14.8%			2.8%			(23.2%	)		20.4%			12.8%			22.9%
Operating income		17.6%			2.4%			(14.4%	)		21.2%			12.0%			22.7%

See pages 8, 25, 27, 28 and 29 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures.

1. Adjusted for preference share dividend and cancellation of preference shares.

4

Aspen Insurance Holdings Limited

Consolidated Statements of Operations — Year To Date

	Three Months Ended March 31,
(in US$ millions except for percentages)	2009			2008			2007
UNDERWRITING REVENUES
Gross written premiums		$636.8			$596.2			$636.5
Premiums ceded		(130.2	)		(76.6	)		(81.4	)
Net written premiums		506.6			519.6			555.1
Change in unearned premiums		(59.3	)		(128.0	)		(116.1	)
Net earned premiums		447.3			391.6			439.0
UNDERWRITING EXPENSES
Losses and loss expenses		250.8			207.2			225.5
Acquisition expenses		78.6			76.4			77.7
General and administrative expenses		48.5			50.8			45.3
Total underwriting expenses		377.9			334.4			348.5
Underwriting income		69.4			57.2			90.5
OTHER OPERATING REVENUE
Net investment income		59.2			39.1			67.5
Interest expense		(3.9	)		(3.9	)		(4.2	)
Total other operating revenue		55.3			35.2			63.3
Other (expense) income		(2.7	)		(2.2	)		(7.3	)
OPERATING INCOME BEFORE TAX		122.0			90.2			146.5
OTHER
Net realized and unrealized exchange (losses) gains		(2.3	)		4.3			5.5
Net realized and unrealized investment (losses) gains		(12.2	)		1.0			(4.8	)
INCOME BEFORE TAX		107.5			95.5			147.2
Income taxes		(16.1	)		(14.3	)		(25.3	)
NET INCOME AFTER TAX		91.4			81.2			121.9
Dividends paid on ordinary shares		(12.3	)		(12.9	)		(13.2	)
Dividends paid on preference shares		(6.9	)		(6.9	)		(6.9	)
Retained income		$72.2			$61.4			$101.8
Components of net income after tax
Operating income		$105.7			$76.0			$120.6
Net realized and unrealized exchange (losses) gains after tax		(2.3	)		4.3			5.5
Net realized investment (losses) gains after tax		(12.0	)		0.9			(4.2	)
NET INCOME AFTER TAX		$91.4			$81.2			$121.9
Loss ratio		56.1%			52.9%			51.4%
Policy acquisition expense ratio		17.6%			19.5%			17.7%
General and administrative expense ratio		10.8%			13.0%			10.3%
Expense ratio		28.4%			32.5%			28.0%
Combined ratio		84.5%			85.4%			79.4%

See pages 8, 25, 27, 28 and 29 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures.

5

Aspen Insurance Holdings Limited
Consolidated Balance Sheets

	March 31,		December 31,		September 30,		June 30,		March 31,
(in US$ millions, except for per share amounts)	2009		2008		2008		2008		2008
ASSETS
Investments
Fixed maturities		$4,566.6		$4,433.1		$4,410.7		$4,612.7		$4,472.2
Other investments		290.9		286.9		513.1		555.3		544.5
Short-term investments		291.8		224.9		226.3		193.6		309.3
Total investments		5,149.3		4,944.9		5,150.1		5,361.6		5,326.0
Cash and cash equivalents		913.2		809.1		741.6		620.8		695.7
Reinsurance recoverables
Unpaid losses		297.9		283.3		241.5		231.7		276.0
Ceded unearned premiums		138.8		46.3		77.5		98.9		121.8
Receivables
Underwriting premiums		793.6		677.5		675.4		792.0		716.2
Other		44.3		46.5		102.6		79.0		50.3
Funds withheld		71.9		85.0		77.4		76.9		100.0
Deferred policy acquisition costs		166.6		149.7		166.7		167.4		151.6
Derivatives at fair value		7.2		11.8		10.9		11.3		15.4
Receivable for securities sold		5.1		177.2		—		—		—
Office properties and equipment		27.0		33.8		32.4		30.4		28.0
Other assets		16.7		15.5		19.8		20.9		17.7
Intangible assets		8.2		8.2		8.2		8.2		8.2
Total assets		$7,639.8		$7,288.8		$7,304.1		$7,499.1		$7,506.9
LIABILITIES
Insurance reserves
Losses and loss adjustment expenses		$3,096.2		$3,070.3		$3,081.9		$2,944.4		$2,950.3
Unearned premiums		963.8		810.7		940.8		1,018.9		930.1
Total insurance reserves		4,060.0		3,881.0		4,022.7		3,963.3		3,880.4
Payables
Reinsurance premiums		197.1		103.0		98.0		115.6		133.1
Taxation		84.6		72.6		33.4		82.6		114.3
Accrued expenses and other payables		206.7		192.5		246.2		219.7		189.6
Liabilities under derivative contracts		9.4		11.1		16.7		14.5		17.3
Total payables		497.8		379.2		394.3		432.4		454.3
Long-term debt		249.6		249.5		249.5		249.5		249.5
Total liabilities		4,807.4		4,509.7		4,666.5		4,645.2		4,584.2
SHAREHOLDERS’ EQUITY
Ordinary shares		0.1		0.1		0.1		0.1		0.1
Preference shares		—		—		—		—		—
Additional paid-in capital		1,749.9		1,754.8		1,754.1		1,753.3		1,849.5
Retained earnings		956.9		884.7		882.1		1,027.3		920.2
Accumulated other comprehensive income, net of taxes		125.5		139.5		1.3		73.2		152.9
Total shareholders’ equity		2,832.4		2,779.1		2,637.6		2,853.9		2,922.7
Total liabilities and shareholders’ equity		$7,639.8		$7,288.8		$7,304.1		$7,499.1		$7,506.9
Book value per ordinary share		$29.85		$28.85		$27.14		$29.84		$29.22

See pages 8, 25, 27, 28 and 29 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures.

6

Aspen Insurance Holdings Limited

Earnings Per Share and Book Value Per Share

	Three Months Ended
	March 31,		March 31,
(in US$ except for number of shares)	2009		2008
Basic earnings per ordinary share
Net income adjusted for preference share dividend and cancellation of preference shares		$1.42		$0.87
Operating income adjusted for preference share dividend		$1.21		$0.81
Diluted earnings per ordinary share
Net income adjusted for preference share dividend and cancellation of preference shares		$1.39		$0.85
Operating income adjusted for preference share dividend		$1.18		$0.79
Weighted average number of ordinary shares outstanding (in millions)		81.535		85.511
Weighted average number of ordinary shares outstanding and dilutive potential ordinary shares (in millions)		83.572		87.957
Book value per ordinary share		$29.85		$29.22
Diluted book value per ordinary share (treasury stock method)		$29.12		$28.48
Ordinary shares outstanding at end of the period (in millions)		82.763		85.395
Ordinary shares outstanding and dilutive potential ordinary shares at end of the period (treasury stock method) (in millions)		84.832		87.607

See pages 8, 25, 27, 28 and 29 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures.

7

Aspen Insurance Holdings Limited

Return On Average Equity

	Three Months Ended
(in US$ millions except for percentages)	March 31, 2009			March 31, 2008
Closing shareholders’ equity	$	2,832.4			$2,922.7
Average adjustment		(561.9	)		(604.5	)
Average equity (1)	$	2,270.5			$2,318.2
Return on average equity:
Net income adjusted for preference share dividend		3.7%			3.2%
Operating income adjusted for preference share dividend		4.4%			3.0%
Annualized return on average equity:
Net income		14.8%			12.8%
Operating income		17.6%			12.0%
Components of return on average equity:
Return on average equity from underwriting activity (2)		3.1%			2.5%
Return on average equity from investment and other activity (3)		2.0%			1.1%
Pre-tax operating income return on average equity		5.1%			3.6%
Post-tax operating income return on average equity (4)		4.4%			3.0%

See pages 8, 25, 27, 28 and 29 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures.

1.   Average equity is calculated by taking the simple average at latest quarter end and the previous quarter end of the closing shareholders’ equity excluding (i) preference shares, (ii) after-tax unrealized appreciation or depreciation on investments and (iii) the average after-tax unrealized foreign exchange gains and losses.

2.	Calculated by using underwriting income.
3.	Calculated by using total other operating revenue and other income/expense adjusted for preference share dividend.
4.	Calculated by using operating income after-tax adjusted for preference share dividend.

8

Aspen Insurance Holdings Limited

Consolidated Underwriting Results by Operating Segment

	Three Months Ended March 31, 2009										Three Months Ended March 31, 2008
	Property		Casualty		International		U.S.				Property		Casualty		International		U.S.
(in US$ millions except for percentages)	Reinsurance		Reinsurance		Insurance		Insurance		Total		Reinsurance		Reinsurance		Insurance		Insurance			Total
Gross written premiums		$220.5		$186.8		$194.7		$34.8		$636.8		$184.2		$182.1		$199.3		$30.6			$596.2
Net written premiums		182.1		185.8		124.8		13.9		506.6		175.4		180.0		142.0		22.2			519.6
Gross earned premiums		150.9		110.0		198.8		33.5		493.2		140.3		95.7		165.3		26.0			427.3
Net earned premiums		139.1		109.5		175.0		23.7		447.3		127.0		94.7		150.2		19.7			391.6
Losses and loss expenses		40.2		72.2		127.0		11.4		250.8		38.0		61.5		97.7		10.0			207.2
Policy acquisition expenses		24.8		21.9		28.0		3.9		78.6		25.9		17.7		28.0		4.8			76.4
Operating and administration expenses		15.2		9.0		18.6		5.7		48.5		16.6		10.7		17.9		5.6			50.8
Underwriting income (loss)		$58.9		$6.4		$1.4		$2.7		$69.4		$46.5		$4.8		$6.6		$(0.7	)		$57.2
Net reserves for loss and loss adjustment expenses		$402.8		$1,322.9		$950.4		$122.2		$2,798.3		$424.7		$1,302.5		$883.9		$63.2			$2,674.3
RATIOS
Loss ratio		28.9%		65.9%		72.6%		48.1%		56.1%		29.9%		64.9%		65.0%		50.8%			52.9%
Policy acquisition expense ratio		17.8%		20.0%		16.0%		16.5%		17.6%		20.4%		18.7%		18.6%		24.3%			19.5%
Operating and administration expense ratio		10.9%		8.2%		10.6%		24.1%		10.8%		13.1%		11.3%		11.9%		28.4%			13.0%
Expense ratio		28.7%		28.2%		26.6%		40.6%		28.4%		33.5%		30.0%		30.5%		52.7%			32.5%
Combined ratio		57.6%		94.1%		99.2%		88.7%		84.5%		63.4%		94.9%		95.5%		103.6%			85.4%

9

Aspen Insurance Holdings Limited

Property Reinsurance Segment — Quarterly Results

(in US$ millions except for percentages)	Q1 2009		Q4 2008		Q3 2008			Q2 2008		Q1 2008		Q1 2007
Gross written premiums		$220.5		$81.5		$152.8			$170.5		$184.2		$192.1
Net written premiums		182.1		83.0		140.2			165.5		175.4		177.1
Gross earned premiums		150.9		155.3		152.3			144.5		140.3		161.3
Net earned premiums		139.1		143.0		138.8			123.6		127.0		153.4
Net losses and loss expenses		40.2		73.8		164.6			38.3		38.0		64.1
Policy acquisition expenses		24.8		32.1		23.4			23.6		25.9		27.4
Operating and administrative expenses		15.2		16.0		14.7			18.4		16.6		14.5
Underwriting income (loss)		$58.9		$21.1		$(63.9	)		$43.3		$46.5		$47.4
RATIOS
Loss ratio		28.9%		51.6%		118.6%			31.0%		29.9%		41.8%
Policy acquisition expense ratio		17.8%		22.4%		16.8%			19.1%		20.4%		17.9%
Operating and administrative expense ratio		10.9%		11.2%		10.6%			14.9%		13.1%		9.4%
Expense ratio		28.7%		33.6%		27.4%			34.0%		33.5%		27.3%
Combined ratio		57.6%		85.2%		146.0%			65.0%		63.4%		69.1%

10

Aspen Insurance Holdings Limited

Casualty Reinsurance Segment — Quarterly Results

(in US$ millions except for percentages)	Q1 2009		Q4 2008		Q3 2008		Q2 2008		Q1 2008		Q1 2007
Gross written premiums		$186.8		$97.7		$79.7		$56.8		$182.1		$223.3
Net written premiums		185.8		98.7		79.8		54.5		180.0		216.6
Gross earned premiums		110.0		121.3		113.7		87.7		95.7		111.0
Net earned premiums		109.5		120.1		112.9		85.8		94.7		106.4
Losses and loss expenses		72.2		80.5		75.9		54.3		61.5		60.8
Policy acquisition expenses		21.9		19.4		16.6		11.7		17.7		19.3
Operating and administration expenses		9.0		10.4		9.6		12.5		10.7		9.9
Underwriting income		$6.4		$9.8		$10.8		$7.3		$4.8		$16.4
RATIOS
Loss ratio		65.9%		67.1%		67.2%		63.3%		64.9%		57.2%
Policy acquisition expense ratio		20.0%		16.2%		14.7%		13.6%		18.7%		18.1%
Operating and administration expense ratio		8.2%		8.7%		8.5%		14.6%		11.3%		9.3%
Expense ratio		28.2%		24.9%		23.2%		28.2%		30.0%		27.4%
Combined ratio		94.1%		92.0%		90.4%		91.5%		94.9%		84.6%

11

Aspen Insurance Holdings Limited

International Insurance Segment — Quarterly Results

(in US$ millions except for percentages)	Q1 2009		Q4 2008			Q3 2008			Q2 2008		Q1 2008		Q1 2007
Gross written premiums		$194.7		$228.8			$180.8			$258.9		$199.3		$185.3
Net written premiums		124.8		202.0			162.2			251.6		142.0		139.9
Gross earned premiums		198.8		228.9			185.4			178.6		165.3		162.8
Net earned premiums		175.0		190.1			158.6			162.9		150.2		146.8
Losses and loss expenses		127.0		150.4			141.8			83.6		97.7		81.3
Policy acquisition expenses		28.0		32.9			26.5			26.0		28.0		25.4
Operating and administration expenses		18.6		16.2			21.1			19.2		17.9		14.7
Underwriting income (loss)		$1.4		$(9.4	)		$(30.8	)		$34.1		$6.6		$25.4
RATIOS
Loss ratio		72.6%		79.1%			89.4%			51.3%		65.0%		55.4%
Policy acquisition expense ratio		16.0%		17.3%			16.7%			16.1%		18.6%		17.3%
Operating and administration expense ratio		10.6%		8.5%			13.3%			11.8%		11.9%		10.0%
Expense ratio		26.6%		25.8%			30.0%			27.9%		30.5%		27.3%
Combined ratio		99.2%		104.9%			119.4%			79.2%		95.5%		82.7%

12

Aspen Insurance Holdings Limited

U.S. Insurance Segment — Quarterly Results

(in US$ millions except for percentages)	Q1 2009		Q4 2008		Q3 2008			Q2 2008		Q1 2008			Q1 2007
Gross written premiums		$34.8		$27.4		$28.0			$42.6		$30.6			$35.7
Net written premiums		13.9		22.5		21.6			34.4		22.2			21.5
Gross earned premiums		33.5		33.0		31.5			29.6		26.0			38.9
Net earned premiums		23.7		25.4		23.9			25.0		19.7			32.4
Losses and loss expenses		11.4		5.9		31.1			12.1		10.0			19.3
Policy acquisition expenses		3.9		3.1		3.9			3.7		4.8			5.6
Operating and administration expenses		5.7		6.0		6.2			7.0		5.6			6.2
Underwriting income (loss)		$2.7		$10.4		$(17.3	)		$2.2		$(0.7	)		$1.3
RATIOS
Loss ratio		48.1%		23.2%		130.1%			48.4%		50.8%			59.6%
Policy acquisition expense ratio		16.5%		12.3%		16.3%			14.7%		24.3%			17.3%
Operating and administration expense ratio		24.1%		23.5%		25.7%			27.9%		28.4%			19.1%
Expense ratio		40.6%		35.8%		42.0%			42.6%		52.7%			36.4%
Combined ratio		88.7%		59.0%		172.1%			91.0%		103.6%			96.0%

13

Aspen Insurance Holdings Limited

Gross Written Premiums By Segment And Line Of Business

(in US$ millions)	Q1 2009		Q4 2008			Q3 2008		Q2 2008		Q1 2008		Q1 2007
PROPERTY REINSURANCE
Treaty Catastrophe		$116.7		$(2.8	)		$65.0		$79.2		$111.6		$118.6
Treaty Risk Excess		31.3		5.9			36.3		40.0		29.9		23.0
Treaty Pro Rata		48.2		68.9			36.5		36.5		32.7		42.0
Property Facultative		17.0		9.5			15.0		14.8		10.0		8.5
Credit and Surety		7.3		—			—		—		—		—
		$220.5		$81.5			$152.8		$170.5		$184.2		$192.1
CASUALTY REINSURANCE
U.S. Treaty		$106.3		$80.2			$60.1		$46.9		$89.6		$131.3
International Treaty		77.0		13.3			15.3		5.7		89.5		88.4
Casualty Facultative		3.5		4.2			4.3		4.2		3.0		3.6
		$186.8		$97.7			$79.7		$56.8		$182.1		$223.3
INTERNATIONAL INSURANCE
Marine and Specialty Liability		$50.8		$45.0			$14.1		$47.4		$54.8		$54.5
Energy Property		16.4		7.5			22.3		41.7		23.4		28.2
Marine Hull		16.5		19.1			10.7		17.5		18.6		16.4
Aviation		10.4		48.2			19.3		23.1		11.2		10.8
U.K. Commercial Property		7.4		5.7			14.1		22.7		9.4		7.5
U.K. Commercial Liability		9.1		14.6			23.3		17.1		20.1		22.0
Non-Marine and Transportation Liability		7.9		10.9			8.7		14.3		7.1		—
Professional Liability		7.7		15.7			13.3		7.4		7.6		—
Excess Casualty		4.8		12.4			8.9		6.3		2.0		—
Financial Institutions		3.7		11.1			15.8		9.2		2.9		—
Financial and Political Risks		9.2		7.8			5.5		21.3		4.5		—
U.K. Commercial Property-Construction		3.5		2.9			4.4		4.5		—		—
Management and Technology Liability		1.8		3.5			—		—		—		—
Specialty Reinsurance		45.5		24.4			20.4		26.4		37.7		46.0
		$194.7		$228.8			$180.8		$258.9		$199.3		$185.4
U.S. INSURANCE
Property		$14.4		$10.9			$10.7		$21.1		$10.5		$12.4
Casualty		20.4		16.5			17.3		21.5		20.1		23.3
		$34.8		$27.4			$28.0		$42.6		$30.6		$35.7
TOTAL GROSS WRITTEN PREMIUMS		$636.8		$435.4			$441.3		$528.8		$596.2		$636.5

14

Aspen Insurance Holdings Limited

Accident Year Loss Ratios

	Three Months Ended March 31, 2009														Three Months Ended March 31, 2008
	Property			Casualty			International		U.S.						Property			Casualty			International			U.S.
	Reinsurance			Reinsurance			Insurance		Insurance			Total			Reinsurance			Reinsurance			Insurance			Insurance			Total
BEFORE ACCIDENT YEAR ADJUSTMENT
Loss ratio		28.9%			65.9%			72.6%		48.1%			56.1%			29.9%			64.9%			65.0%			50.8%			52.9%
Policy acquisition expense ratio		17.8%			20.0%			16.0%		16.5%			17.6%			20.4%			18.7%			18.6%			24.3%			19.5%
Operating and administration expense ratio		10.9%			8.2%			10.6%		24.1%			10.8%			13.1%			11.3%			11.9%			28.4%			13.0%
Expense ratio		28.7%			28.2%			26.6%		40.6%			28.4%			33.5%			30.0%			30.5%			52.7%			32.5%
Combined ratio		57.6%			94.1%			99.2%		88.7%			84.5%			63.4%			94.9%			95.5%			103.6%			85.4%
ACCIDENT YEAR ADJUSTMENT
Loss ratio		8.4%			9.2%			3.7%		8.9%			6.9%			11.1%			11.6%			6.1%			26.6%			10.2%
Policy acquisition expense ratio		(0.9%	)		(0.6%	)		0.7%		(0.2%	)		(0.2%	)		0.1%			(0.2%	)		0.1%			(0.1%	)		—
Operating and administration expense ratio		1.1%			0.8%			0.7%		(0.1%	)		0.9%			(0.8%	)		(0.7%	)		(0.8%	)		1.7%			(0.7%	)
Expense ratio		0.2%			0.2%			1.4%		(0.3%	)		0.7%			(0.7%	)		(0.9%	)		(0.7%	)		1.6%			(0.7%	)
Combined ratio		8.6%			9.4%			5.1%		8.6%			7.6%			10.4%			10.7%			5.4%			28.2%			9.5%
ACCIDENT YEAR RATIOS
Current accident year loss ratio		37.3%			75.1%			76.3%		57.0%			63.0%			41.0%			76.5%			71.1%			77.4%			63.1%
Policy acquisition expense ratio		16.9%			19.4%			16.7%		16.3%			17.4%			20.5%			18.5%			18.7%			24.2%			19.5%
Operating and administration expense ratio		12.0%			9.0%			11.3%		24.0%			11.7%			12.3%			10.6%			11.1%			30.1%			12.3%
Expense ratio		28.9%			28.4%			28.0%		40.3%			29.1%			32.8%			29.1%			29.8%			54.3%			31.8%
Combined ratio		66.2%			103.5%			104.3%		97.3%			92.1%			73.8%			105.6%			100.9%			131.7%			94.9%

15

Aspen Insurance Holdings Limited

Consolidated Statements of Changes in Shareholders’ Equity

	Three Months Ended March 31,
(in US$ millions)	2009			2008
Ordinary shares
Beginning and end of period		$0.1			$0.1
Preference shares
Beginning and end of period		—			—
Additional paid-in capital
Beginning of period		1,754.8			1,846.1
New shares issued		25.1			—
Preference shares repurchased		(34.1	)		—
Share-based compensation		4.1			3.4
End of period		1,749.9			1,849.5
Retained earnings
Beginning of period		884.7			858.8
Net income for the period		91.4			81.2
Dividends paid on ordinary and preference shares		(19.2	)		(19.8	)
End of period		956.9			920.2
Accumulated other comprehensive income:
Cumulative foreign currency translation adjustments, net of taxes:
Beginning of period		87.6			80.2
Change for the period		(15.2	)		5.4
End of period		72.4			85.6
Loss on derivatives
Beginning and end of period		(1.4	)		(1.6	)
Unrealized appreciation (depreciation) on investments, net of taxes:
Beginning of period		53.3			34.0
Change for the period		1.2			34.9
End of period		54.5			68.9
Total accumulated other comprehensive income		125.5			152.9
Total shareholders’ equity		$2,832.4			$2,922.7

16

Aspen Insurance Holdings Limited

Consolidated Statements of Comprehensive Income

	Three Months Ended March 31,
(in US$ millions)	2009			2008
Net income		$91.4			$81.2
Other comprehensive (loss) income, net of taxes:
Reclassification adjustment for net realized losses included in net income		4.1			(0.8	)
Change in net unrealized gains and losses on available for sale securities held		(2.9	)		35.7
Change in foreign currency translation adjustment		(15.2	)		5.4
Other comprehensive income		(14.0	)		40.3
Comprehensive income		$77.4			$121.5

17

Aspen Insurance Holdings Limited

Condensed Consolidated Statements of Cash Flows

	Three Months Ended March 31,
(in US$ millions)	2009			2008
Net cash from/(used in) operating activities	$	203.2		$	163.5
Net cash from/(used in) investing activities		(53.2	)		(73.5	)
Net cash from/(used in) financing activities		(28.2	)		(19.8	)
Effect of exchange rate movements on cash and cash equivalents		(17.7	)		(25.9	)
Increase in cash and cash equivalents		104.1			44.3
Cash at beginning of the period		809.1			651.4
Cash at end of the period	$	913.2		$	695.7

18

Aspen Insurance Holdings Limited

Reserves For Losses And Loss Expenses

	As At			As At
	March 31,			December 31,
(in US$ millions)	2009			2008
Provision for losses and loss expenses at start of period	$	3,070.3		$	2,946.0
Less reinsurance recoverable		(283.3	)		(304.7	)
Net loss and loss expenses at start of period		2,787.0			2,641.3
Net loss and loss expenses (disposed) acquired		(11.7	)		(27.8	)
Provision for losses and loss expenses for claims incurred
Current period		260.6			1,203.0
Prior period release		(9.8	)		(83.5	)
Total incurred		250.8			1,119.5
Losses and loss expense payments for claims incurred		(138.8	)		(727.0	)
Foreign exchange (gains) losses		(89.0	)		(219.0	)
Net loss and loss expense reserves at end of period		2,798.3			2,787.0
Plus reinsurance recoverables on unpaid losses at end of period		297.9			283.3
Gross loss and loss expense reserves at end of period	$	3,096.2		$	3,070.3

19

Aspen Insurance Holdings Limited
Reserves By Operating Segment

	As At March 31, 2009							As At December 31, 2008
			Reinsurance							Reinsurance
(in US$ millions)	Gross		Recoverable			Net		Gross		Recoverable			Net
Property Reinsurance		$446.8		$(44.0	)		$402.8		$488.5		$(107.8	)		$380.7
Casualty Reinsurance		1,328.8		(5.9	)		1,322.9		1,311.1		(2.3	)		1,308.8
International Insurance		1,191.6		(241.2	)		950.4		1,117.4		(113.7	)		1,003.7
U.S. Insurance		129.0		(6.8	)		122.2		153.3		(59.5	)		93.8
Total losses and loss expense reserves		$3,096.2		$(297.9	)		$2,798.3		$3,070.3		$(283.3	)		$2,787.0

20

Aspen Insurance Holdings Limited

Prior Year Reserve Releases

	As At March 31, 2009								As At March 31, 2008
				Reinsurance							Reinsurance
(in US$ millions)	Gross			Recoverable		Net			Gross		Recoverable			Net
Property Reinsurance		$6.1			$0.6		$6.7			$4.1		$9.5			$13.6
Casualty Reinsurance		3.1			—		3.1			14.2		0.1			14.3
International Insurance		(8.6	)		6.6		(2.0	)		5.0		1.9			6.9
U.S. Insurance		0.7			1.3		2.0			6.3		(1.6	)		4.7
Release in reserves for prior years during the period		$1.3			$8.5		$9.8			$29.6		$9.9			$39.5

21

Aspen Insurance Holdings Limited

Ratings Of Reinsurers

(in US$ millions except for percentages)	As at March 31, 2009			As at December 31, 2008
S&P
AAA		$16.0	5.4%		$15.9	5.6%
AA−		59.8	20.1%		103.7	36.6%
A+		152.8	51.3%		98.8	34.9%
A		7.0	2.4%		6.9	2.4%
A−		30.2	10.1%		28.7	10.1%
Fully collateralized		2.5	0.8%		2.5	0.9%
Not rated		29.6	9.9%		26.8	9.5%
		$297.9	100.0%		$283.3	100.0%
A.M. Best
A++		$16.1	5.4%		$15.9	5.6%
A+		25.8	8.7%		67.2	23.7%
A		215.0	72.2%		161.9	57.1%
A−		29.0	9.7%		28.6	10.1%
Fully collateralized		2.5	0.8%		2.5	0.9%
Not rated		9.5	3.2%		7.2	2.6%
		$297.9	100.0%		$283.3	100.0%

22

Aspen Insurance Holdings Limited

Consolidated Investment Portfolio

	As At March 31, 2009									Percentage Of Total Fair Value
			Gross		Gross					As At		As At		As At
	Amortized		Unrealized		Unrealized					March 31,		December 31,		December 31,
(in US$ millions except for percentages)	Cost		Gains		Losses			Fair Value		2009		2008		2007
MARKETABLE SECURITIES — AVAILABLE FOR SALE
U.S. government		$623.6		$41.5		—			$665.1		10.9%		10.9%		10.9%
U.S. government agency securities		367.9		27.9		(0.3	)		395.5		6.5%		6.6%		5.6%
Municipal securities		7.7		0.4		—			8.1		0.1%		0.1%		—
Corporate securities		1,567.9		32.5		(49.8	)		1,550.6		25.5%		23.8%		25.6%
Foreign government		328.9		20.8		—			349.7		5.7%		6.4%		7.2%
Asset-backed securities		179.2		1.1		(2.3	)		178.0		2.9%		3.4%		3.8%
Mortgage-backed securities		1,307.7		41.6		(42.7	)		1,306.6		21.4%		22.9%		20.8%
Total fixed maturities		4,382.9		165.8		(95.1	)		4,453.6		73.0%		74.1%		73.9%
Short-term investments		289.8		—		—			289.8		4.8%		3.8%		4.8%
Total Available For Sale		$4,672.7		$165.8		$(95.1	)		$4,743.4		77.8%		77.9%		78.7%
MARKETABLE SECURITIES — TRADING
Corporate securities		111.5		0.8		(0.4	)		111.9		1.8%		—		—
Foreign government		0.9		0.2		—			1.1		—		—		—
Total fixed maturities		112.4		1.0		(0.4	)		113.0		1.8%		—		—
Short-term investments		2.0		—		—			2.0		0.1%		—		—
Total Trading		$114.4		$1.0		$(0.4	)		$115.0		1.9%		—		—
OTHER INVESTMENTS									$290.9		4.8%		4.9%		9.5%
Cash									913.2		15.0%		13.5%		11.0%
Accrued interest									31.0		0.5%		3.7%		0.8%
TOTAL CASH AND ACCRUED INTEREST									$944.2		15.5%		17.2%		11.8%
Total Cash and Investments									$6,093.5		100.0%		100.0%		100.0%

23

Aspen Insurance Holdings Limited

Investment Analysis

(in US$ millions except for percentages)	Q1 2009			Q4 2008			Q3 2008			Q2 2008			Q1 2008
Net investment income from fixed income investments and cash		$55.2			$59.3			$61.5			$59.7			$56.0
Net investment income (loss) from investments accounted for by the equity method		4.0			(49.0	)		(42.2	)		10.8			(16.9	)
Net investment income		59.2			10.3			19.3			70.5			39.1
Net realized investment (losses) gains		(12.2	)		8.4			(58.1	)		0.8			1.0
Change in unrealized gains (losses) on investments (gross of tax)		3.3			138.3			(46.6	)		(110.4	)		44.4
Total return on investments		$50.3			$157.0			$(85.4	)		$(39.1	)		$84.5
PORTFOLIO CHARACTERISTICS
Fixed income portfolio book yield		4.42%			4.64%			4.87%			4.84%			4.90%
Fixed income portfolio duration		2.90 years			3.12 years			3.51 years			3.58 years			3.35 years

24

Aspen Insurance Holdings Limited

Book Value Per Ordinary Share

(in US$ millions except for number of shares)	March 31, 2009			December 31, 2008			September 30, 2008			June 30, 2008			March 31, 2008
Net assets		$2,832.4			$2,779.1			$2,637.6			$2,853.9			$2,922.7
Less: Intangible assets		(8.2	)		(8.2	)		(8.2	)		(8.2	)		(8.2	)
Preference shares		(353.6	)		(419.2	)		(419.2	)		(419.2	)		(419.2	)
Total		$2,470.6			$2,351.7			$2,210.2			$2,426.5			$2,495.3
Ordinary shares outstanding (in millions)		82.763			81.507			81.450			81.321			85.395
Ordinary shares and dilutive potential ordinary shares (in millions)		84.832			83.706			84.325			83.691			87.607
Book value per ordinary share		$29.85			$28.85			$27.14			$29.84			$29.22
Diluted book value per ordinary share (treasury stock method)		$29.12			$28.10			$26.21			$28.99			$28.48

The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company’s ordinary shares at the average market price during the period of calculation.

25

Aspen Insurance Holdings Limited

Diluted Share Analysis

	Three Months Ended March 31,
	2009		2008
WEIGHTED AVERAGE ORDINARY SHARES OUTSTANDING (millions)
Basic		81.535		85.511
Dilutive share equivalents:
Employee options		0.645		1.357
Options issued to Appleby Trust (Bermuda) Limited (Names Trust)		0.335		0.203
Performance shares		0.872		0.661
Restricted share units		0.185		0.225
Weighted average diluted shares outstanding		83.572		87.957

The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company’s ordinary shares at the average market price during the period of calculation.

26

Aspen Insurance Holdings Limited

Operating Income Reconciliation

Net income is adjusted to exclude after tax net foreign exchange gains and losses, realized gains and losses in investments and preference share repurchase gain.

	Three Months Ended
(in US$ millions except where stated)	March 31, 2009			March 31, 2008
Net income as reported		$91.4			$81.2
Preference share dividends		(6.9	)		(6.9	)
Preference share repurchase gain		31.5			—
Net income available to ordinary shareholders		116.0			74.3
Add (deduct) after tax income:
Net foreign exchange losses (gains)		2.3			(4.3	)
Net realized losses (gains) on investments		12.0			(0.9	)
Preference share repurchase (gain)		(31.5	)		—
Operating income after tax available to ordinary shareholders		98.8			69.1
Tax on operating income		16.3			14.2
Operating income before tax available to ordinary shareholders		$115.1			$83.3
WEIGHTED AVERAGE ORDINARY SHARES OUTSTANDING (millions)
Basic		81.535			85.511
Dilutive share equivalents:
Employee options		0.645			1.357
Options issued to Appleby Trust (Bermuda) Limited (Names Trust)		0.335			0.203
Performance shares		0.872			0.661
Restricted share units		0.185			0.225
Weighted average diluted shares outstanding		83.572			87.957
BASIC EARNINGS PER ORDINARY SHARE
Net income adjusted for preference share dividend and cancellation of preference shares		$1.42			$0.87
Add (deduct) after tax income:
Net foreign exchange losses (gains)		0.03			(0.05	)
Net realized gains (losses) on investments		0.15			(0.01	)
Preference share repurchase (gain)		(0.39	)		—
Operating income adjusted for preference shares dividend		$1.21			$0.81
DILUTED EARNINGS PER ORDINARY SHARE
Net income adjusted for preference share dividend and cancellation of preference shares		$1.39			$0.85
Add (deduct) after tax income:
Net foreign exchange losses (gains)		0.03			(0.05	)
Net realized gains (losses) on investments		0.14			(0.01	)
Preference share repurchase (gain)		(0.38	)		—
Operating income adjusted for preference shares dividend		$1.18			$0.79

27

Aspen Insurance Holdings Limited

Net Income Reconciliation

Net income is adjusted to exclude after-tax net income or losses from investments accounted for using the equity method and the gain on repurchase of preference shares. These investments represent our investments in funds of hedge funds. According to the equity method, gains and losses on the hedge funds are recognized through the income statement.

	Three Months Ended			Three Months Ended
(in US$ millions except where stated)	March 31, 2009			March 31, 2008
Net income available to ordinary shareholders		$116.0			$74.3
Add (deduct) after tax income:
Loss (income) from investments accounted for by the equity method		(4.0	)		16.9
Tax on income/loss from investments accounted for by the equity method		0.3			(2.5	)
Preference share repurchase (gain)		(31.5	)		—
Adjusted net income		$80.8			$88.7
WEIGHTED AVERAGE ORDINARY SHARES OUTSTANDING (millions)
Basic		81.535			85.511
Dilutive share equivalents:
Employee options		0.645			1.357
Options issued to Appleby Trust (Bermuda) Limited (Names Trust)		0.335			0.203
Performance shares		0.872			0.661
Restricted share units		0.185			0.225
Weighted average diluted shares outstanding		83.572			87.957
BASIC EARNINGS PER ORDINARY SHARE
Net income adjusted for preference share dividend and cancellation of preference shares		$1.42			$0.87
Add (deduct) after tax income:
Loss (income) from investments accounted for by the equity method		(0.05	)		0.20
Tax on income/loss from investments accounted for by the equity method		—			(0.03	)
Preference share repurchase (gain)		(0.39	)		—
Adjusted net income per share		$0.98			$1.04
DILUTED EARNINGS PER ORDINARY SHARE
Net income adjusted for preference share dividend and cancellation of preference shares		$1.39			$0.85
Add (deduct) after tax income:
Loss (income) from investments accounted for by the equity method		(0.05	)		0.19
Tax on income/loss from investments accounted for by the equity method		—			(0.03	)
Preference share repurchase (gain)		(0.38	)		—
Adjusted net income per share		$0.96			$1.01

28

Aspen Insurance Holdings Limited

Adjusted Operating Income Reconciliation

Net income is adjusted to exclude after-tax net foreign exchange gains and losses, after tax realized gains and losses on investments, after tax net gains and losses from our investments in funds of hedge funds and preference share repurchase gain.

	Three Months Ended
(in US$ millions except where stated)	March 31, 2009			March 31, 2008
Net income available to ordinary shareholders		$116.0			$74.3
Add (deduct) after tax income:
Net foreign exchange losses (gains)		2.3			(4.3	)
Net realized (gains) losses on investments		12.0			(0.9	)
Loss (income) from investments accounted for by the equity method		(3.7	)		14.4
Preference share repurchase (gain)		(31.5	)		—
Adjusted operating income adjusted for preference share dividend		$95.1			$83.5
WEIGHTED AVERAGE ORDINARY SHARES OUTSTANDING (millions)
Basic		81.535			85.511
Dilutive share equivalents:
Employee Options		0.645			1.357
Options issued to Appleby Trust (Bermuda) Limited (Names Trust)		0.335			0.203
Performance Shares		0.872			0.661
Restricted share units		0.185			0.225
Weighted average diluted shares outstanding		83.572			87.957
BASIC EARNINGS PER ORDINARY SHARE
Net income adjusted for preference share dividend and cancellation of preference shares		$1.42			$0.87
Add (deduct) after tax income:
Net foreign exchange losses (gains)		0.03			(0.05	)
Net realized (losses) gains on investments		0.15			(0.01	)
Loss (income) from investments accounted for by the equity method		(0.05	)		0.17
Preference share repurchase (gain)		(0.39	)		—
Adjusted operating income adjusted for preference share dividend		$1.16			$0.98
DILUTED EARNINGS PER ORDINARY SHARE
Net income adjusted for preference share dividend and cancellation of preference shares		$1.39			$0.85
Add (deduct) after tax income:
Net foreign exchange losses (gains)		0.03			(0.05	)
Net realized (losses) gains on investments		0.14			(0.01	)
Loss (income) from investments accounted for by the equity method		(0.04	)		0.16
Preference share repurchase (gain)		(0.38	)		—
Adjusted operating income adjusted for preference share dividend		$1.14			$0.95

29

EX-99.3

Exhibit 99.3

Aspen Insurance Holdings Limited April 30, 2009 Q1 2009 Earnings Conference Call AHL: NYSE

Safe Harbor Disclosure This slide presentation is for information purposes only. It should be read in conjunction with our financial supplement posted on our website on the Investor Relations page and with other documents filed or to be filed shortly by Aspen Insurance Holdings Limited (the "Company" or "Aspen") with the U.S. Securities and Exchange Commission. Non-GAAP Financial Measures In presenting Aspen's results, management has included and discussed certain "non-GAAP financial measures", as such term is defined in Regulation G. Management believes that these non-GAAP measures, which may be defined differently by other companies, better explain Aspen's results of operations in a manner that allows for a more complete understanding of the underlying trends in Aspen's business. However, these measures should not be viewed as a substitute for those determined in accordance with GAAP. The reconciliation of such non-GAAP financial measures to their respective most directly comparable GAAP financial measures in accordance with Regulation G is included herein or in the financial supplement, as applicable, which can be obtained from the Investor Relations section of Aspen's website at www.aspen.bm. Application of the Safe Harbor of the Private Securities Litigation Reform Act of 1995: This presentation contains, and Aspen's earnings conference call will contain, written or oral "forward-looking statements" within the meaning of the U.S. federal securities laws. These statements are made pursuant to the safe harbor provisions of the Private Securities Litigation Reform Act of 1995. Forward-looking statements include all statements that do not relate solely to historical or current facts, and can be identified by the use of words such as "expect," "intend," "plan," "believe," "project," "anticipate," "seek," "will," "estimate," "may," "continue," "guidance," and similar expressions of a future or forward-looking nature. All forward-looking statements address matters that involve risks and uncertainties. Accordingly, there are or will be important factors that could cause actual results to differ materially from those indicated in these statements. Aspen believes these factors include, but are not limited to: the continuing and uncertain impact of the current depressed credit environment, the banking crises and economic recessions in many of the countries in which we operate and of the measures being taken by governments to counter these issues; the risk of a material decline in the value or liquidity of all or parts of our investment portfolio; changes in insurance and reinsurance market conditions that could adversely impact execution of the business plan; changes in our ability to exercise capital management or strategic initiatives or to arrange banking facilities as a result of prevailing market changes or changes in our financial position; our ability to execute our business plan to enter new markets, introduce new products and develop new distribution channels, including their integration into our existing operations; increased counterparty risk due to the impairment of financial institutions; changes in the total industry losses, or our share of total industry losses, resulting from past events such as Hurricanes Ike and Gustav and, with respect to such events, our reliance on loss reports received from cedants and loss adjustors, our reliance on industry loss estimates and those generated by modeling techniques, changes in rulings on flood damage or other exclusions as a result of prevailing lawsuits and case law, any changes in our reinsurers' credit quality and the amount and timing of reinsurance recoverables; the impact of acts of terrorism and related legislation and acts of war; the possibility of greater frequency or severity of claims and loss activity, including as a result of natural or man-made catastrophic events, than our underwriting, reserving, reinsurance purchasing or investment practices have anticipated; evolving interpretive issues with respect to coverage after major loss events; the level of inflation in repair costs due to limited availability of labor and materials after catastrophes; the effectiveness of our loss limitation methods; changes in the availability, cost or quality of reinsurance or retrocessional coverage; the reliability of, and changes in assumptions to, catastrophe pricing, accumulation and estimated loss models; loss of key personnel; a decline in our operating subsidiaries' ratings with Standard & Poor's ("S&P"), A.M. Best or Moody's Investors Service ("Moody's"); changes in general economic conditions, including inflation, foreign currency exchange rates, interest rates and other factors that could affect our investment portfolio; the number and type of insurance and reinsurance contracts that we wrote at the January 1st and other renewal periods in 2009 and the premium rates available at the time of such renewals within our targeted business lines; increased competition on the basis of pricing, capacity, coverage terms or other factors and the related demand and supply dynamics as contracts come up for renewal; decreased demand for our insurance or reinsurance products and cyclical changes in the insurance and reinsurance sectors; changes in government regulations or tax laws in jurisdictions where we conduct business; and Aspen or its Bermudian subsidiary becoming subject to income taxes in the United States or the United Kingdom.; the effect on insurance markets, business practices and relationships of ongoing litigation, investigations and regulatory activity by insurance regulators and prosecutors. For a more detailed description of these uncertainties and other factors, please see the "Risk Factors" section in Aspen's Annual Reports on Form 10-K as filed with the U.S. Securities and Exchange Commission on February 26, 2009. Aspen undertakes no obligation to publicly update or revise any forward-looking statements, whether as a result of new information, future events or otherwise. Readers are cautioned not to place undue reliance on these forward-looking statements, which speak only as of the dates on which they are made.. In addition, any estimates relating to loss events involve the exercise of considerable judgment and reflect a combination of ground-up evaluations, information available to date from brokers and cedants, market intelligence, initial tentative loss reports and other sources. Due to the complexity of factors contributing to the losses and the preliminary nature of the information used to prepare these estimates, there can be no assurance that Aspen's ultimate losses will remain within the stated amount. 2

Financial Highlights: Q1 2009 3 Quarter Ended March 31 2009 2008 Change Gross Written Premiums 636.8 596.2 6.8%) Net Written Premiums 506.6 519.6 (2.5%)) Net Earned Premiums 447.3 391.6 14.2%) Underwriting Income 69.4 57.2 21.3% Net Investment Income 59.2 39.1 51.4% Net Income after tax 91.4 81.2 12.6% Financial Ratios: Loss Ratio 56.1% 52.9% Expense Ratio 28.4% 32.5% Combined Ratio 84.5% 85.4% Annualized Operating ROE * 17.6% 12.0% Operating EPS (Inc Preference Share Repurchase)* $1.56 $0.79 Book Value Per Share (Includes Inc Preference Share Repurchase) $29.12 $28.48 2.2% (US$ in millions, except per share data) (*) Note: See Aspen's quarterly financial supplement for a reconciliation of operating income to net income and average equity to closing shareholders' equity in the Investor Relations section of Aspen's website at www.aspen.bm

Financial Highlights: Group Summary Q1 2009 Underwriting Revenues GWP Premiums Ceded NWP NEP 2008 Q1 596.4 76.6 519.0 391.6 2009 Q1 636.8 130.2 506.6 447.3 North 45.9 46.9 45 43.9 Underwriting Expenses Losses & Loss Expenses Acquisition Exp General Admin Expenses Total Underwriting Expenses 2008 Q1 207.2 76.4 50.8 334.4 2009 Q1 250.8 78.6 48.0 377.9 North 45.9 46.9 45 43.9 Income Underwriting Income Net Investment Income 2008 Q1 57.2 39.1 2009 Q1 69.4 59.2 North 45.9 46.9 Contribution Operating Income Before Tax Income Before Tax Income After Tax Retained Income 2008 Q1 90.2 95.5 81.2 61.4 2009 Q1 122 108.3 91.4 72.2 North 45.9 46.9 45 43.9 5

Key Performance Metrics: Q1 2009 Revenues Net Earned Premium Investment Income ex FOHF Funds of Hedge Funds 2008 Q1 391.6 56 -16.9 2009 Q1 447.3 55.2 4 North 45.9 99 45 Ratio Analysis Loss Ratio Acquisition Expense Ratio Operating Expense Ratio Combined Ratio 2008 Q1 52.9 19.5 13 85.4 2009 Q1 56.1 17.6 10.8 84.5 North 45.9 99 45 5

Results by Business Segment: Q1 2009 GWP Underwriting Income* Property Re Casualty Re International Insurance US Insurance 2008 Q1 184.2 182.1 199.3 30.6 2009 Q1 220.0 186.8 194.7 34.8 North 45.9 99 45 Property Re Casualty Re International Insurance US Insurance 2008 Q1 46.0 4.8 6.6 -0.7 2009 Q1 58.9 6.4 1.4 2.7 North 45.9 99 7 (*) Underwriting income is calculated as underwriting revenues, less underwriting expenses.

Financial Highlights: Total Investment Return - Q1 2009 Income From Fixed Term Investments and Cash Return on Funds of Hedge Funds Realized Investment Gains/Losses Other Than Temporary Impairment Charges Movement In Unrealized Investment Gains/Losses Total Investment Return Q1 2008 56 -16.9 1 0 45.0 84.5 Q1 2009 55.2 4 3 -15.2 3.3 50.3 North 45.9 99 45 43.9 8

Growth in ROE and Book Value Per Share Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Annualised ROE 0.125 0.204 0.18 0.224 0.229 0.204 0.202 0.228 0.128 0.204 -0.232 0.028 0.148 Diluted BV Per Share* 18.95 19.76 21.41 21.83 22.93 23.63 25.68 27.08 28.48 28.99 26.21 28.1 29.12 BVPS has increased 2.2% since March 31, 2008 and 3.6% since December 31, 2008 9 (*) Note: See Aspen's quarterly financial supplement for a reconciliation of diluted book value per share to basic book value per share, reconciliation of average equity to closing shareholders' equity in the Investor Relations section of Aspen's website at www.aspen.bm 2006 2007 2008 2009

Fixed Income Portfolio by Asset Type (US$ in millions) As at March 31, 2009 9 79% of the Fixed Income Portfolio 'AA' or Better, Total Invested Assets Average 'AA+'

2009 Guidance 10 Initial Guidance February 5, 2009 Revised Guidance April 30, 2009 Gross Written Premium $2 billion +- 5% $2 billion +- 5% % Premium Ceded 10% - 12% of GEP 10% - 12% of GEP Combined Ratio 90% - 96% 88% - 94% Tax Rate 13% to 16% 13% to 16% Cat-Load $170 million (Full Year assuming normal loss experience) $140 million (Full Year assuming normal loss experience)

11 Business Performance and Market Outlook * MEC = Marine, Energy & Construction ** M&T = Management & Technology 1 - Rolling ROAE for the last four quarters 3 - Relative Price Movement for all renewed contracts for YTD 5 - Comparison of 2007/08 actual premium to 2008/09 plan premium 2 - Ratio of Actual to Technical (or modelled) price 4 - Terms and Conditions 6 - 2008/09 Plan PAT figure (in $m) 7 - Outlook

Business Performance and Market Outlook: Key Key Performance Absolute Pricing Relative Price Movement Terms and Conditions Volume change Absolute Scale Outlook Key 1 2 3 4 5 6 7 Excellent Excellent Significantly Up Excellent Significantly Up Very significant Excellent Good Good Up Good Up Significant Good Satisfactory Satisfactory Flat Satisfactory Flat Medium Satisfactory Of Concern Of Concern Down Of Concern Down Small Of Concern Unsatisfactory Unsatisfactory Significantly Down Unsatisfactory Significantly Down Very Small Unsatisfactory 12