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): July 30, 2008

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

Exhibit 99.1

Exhibit 99.2

Section 2 — Financial Information

Item 2.02 Results of Operations and Financial Condition

     On July 30, 2008, Aspen Insurance Holdings Limited issued a press release announcing results for the quarter and six months ended June 30, 2008, which has been attached as Exhibit 99.1. In addition, a copy of the Aspen Insurance Holdings Limited Earnings Release Supplement for the quarter and six months ended June 30, 2008 is attached hereto as Exhibit 99.2.

Section 7 — Regulation FD

Item 7.01 Regulation FD Disclosure

     On July 30, 2008, Aspen Insurance Holdings Limited issued a press release announcing results for the quarter and six months ended June 30, 2008, which has been attached as Exhibit 99.1. In addition, a copy of the Aspen Insurance Holdings Limited Earnings Release Supplement for the quarter and six months ended June 30, 2008 is attached hereto as Exhibit 99.2.

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 July 30, 2008.
99.2	Earnings Release Supplement for the quarter and six months ended June 30, 2008.

     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: July 30, 2008	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
SECOND QUARTER AND FIRST HALF 2008 RESULTS

§	Second quarter 2008 net income of $126.9 million, up 10.6% over the same quarter last year.
§	Combined ratio of 78.2% for Q2 2008 versus 88.4% in Q2 2007.
§	Second quarter 2008 net investment income of $70.5 million, up 80.3% from Q1 2008.
§	Annualized operating ROE for the quarter of 21.2% versus 19.7% in Q2 2007.
§	Q2 2008 diluted earnings per share of $1.44 up 26.2% versus $1.14 in Q2 2007.
§	Book value per share of $29.84, up 22.1% versus Q2 2007.

HAMILTON, BERMUDA, July 30, 2008 — Aspen Insurance Holdings Limited (NYSE: AHL) today reported net income for the second quarter of 2008 of $126.9 million and diluted earnings per share of $1.44, an increase of 26.3% over the same quarter last year. The combined ratio was 78.2%, comparing favorably to 88.4% in the same quarter last year. Annualized operating return on equity was 21.2%, an increase of 1.5 percentage points compared with the second quarter of 2007. Book value per share increased 22.1% to $29.84 when compared to the second quarter of 2007.

Second Quarter Financial Highlights

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

(Unaudited)

	Q2 2008			Q2 2007			Change
Gross written premium	$	528.8		$	503.5			5.0	%
Net earned premium	$	397.3		$	451.2			(11.9	)%
Net investment income	$	70.5		$	78.8			(10.5	)%
Net income after tax	$	126.9		$	114.7			10.6	%
Diluted earnings per share	$	1.44		$	1.14			26.3	%
Operating return on equity		21.2	%		19.7	%
Combined ratio		78.2	%		88.4	%
Book value per share	$	29.84		$	24.44			22.1	%
Diluted book value per share	$	28.99		$	23.63			22.7	%

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First Half 2008 Financial Highlights

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

(Unaudited)

	H1 2008			H1 2007			Change
Gross written premium	$	1,125.0		$	1,140.0			(1.3	)%
Net earned premium	$	788.9		$	890.2			(11.4	)%
Net investment income	$	109.6		$	146.3			(25.1	)%
Net income after tax	$	208.1		$	236.6			(12.1	)%
Combined ratio		81.7	%		83.9	%
Operating return on equity		16.6	%		21.1	%
Diluted earnings per share	$	2.23		$	2.40			(7.1	)%

Chris O’Kane, Chief Executive Officer said, “Aspen had a strong quarter and delivered results ahead of our expectations including net income of $126.9 million, operating ROE of 21.2%, EPS of $1.44 and a combined ratio of 78.2%. Our solid underwriting performance demonstrates our well diversified portfolio and stringent risk selection criteria.”

Second Quarter 2008 Operating Highlights

§ Second quarter combined ratio of 78.2% reflects Aspen’s benign catastrophe loss experience against a backdrop of significant industry losses in the U.S. Midwest.

§ Commenced writing business in our new Lloyd’s syndicate, Syndicate 4711.

§ Repurchased $100 million ordinary shares under our share repurchase program.

§ Launch of our Singapore branch at the end of June.

§ $40 million favorable prior year claims development for the quarter across all segments.

§ Improving performance from our U.S. insurance business.

§ Book value per share of $29.84 increased from $24.44 a year ago, up 22.1%.

§ Eleventh consecutive quarterly increase in book value per share, up 2.1% in the quarter.

Business Segment Highlights

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

Property Reinsurance

The property reinsurance segment recorded a combined ratio of 65.0% for the quarter, a 12.3 percentage point improvement over the same period in 2007, with no significant loss activity in the second quarter 2008. On a year to date basis the combined ratio of 64.2% compares favorably to 73.0% recorded in the first half of 2007. Aspen’s exposure to the storms and floods in the U.S. Midwest is within our expectations. The prior year was impacted by catastrophe losses from windstorm Kyrill and the June U.K. Floods. Gross written premium decreased by 10.4% compared with the second quarter of 2007, and 7.2% year to date.

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Casualty Reinsurance

The combined ratio for the quarter for the casualty reinsurance segment improved to 91.5% from 94.7% in the second quarter of 2007. The improvement in the combined ratio was due largely to $24.0 million of reserve releases during the quarter reflecting favorable loss experience from a number of classes in this segment including international casualty and U.S. casualty reinsurance. The combined ratio for the second quarter of 2007 included $4.6 million of reserve strengthening. On an accident year basis the combined ratio for the first half of 2008 was 100.6%. Gross written premium in this segment was down by 28.5% compared to the second quarter of 2007, and down by 21.1% for the first half of this year versus the same period in 2007. The reduction in written premium was primarily due to our rigorous risk selection criteria in challenging market conditions in addition to downward premium adjustments and commutations in our international and U.S. casualty lines.

International Insurance

The international insurance segment reported a combined ratio for the second quarter of 79.2% compared with 88.0% for the same period in 2007. The loss ratio for the segment has improved to 51.3% in the second quarter of 2008 from 61.3% for the second quarter in 2007. This improvement was driven by more favorable loss experience this quarter compared with 2007, which was adversely impacted by large losses on the marine hull and U.K. commercial property business lines during that period. On a year to date basis the combined ratio was 87.1% compared with 85.5% last year. Gross written premium for the quarter was up by 30.2% at $258.9 million, reflecting the incremental contributions from lines of business such as political risk, excess casualty insurance and professional lines.

U.S. Insurance

The combined ratio for the U.S. insurance segment was 91.0%, down significantly from 122.6% for the second quarter of 2007. Year to date, the combined ratio was 96.6%, down from 107.7% in 2007. Gross written premium on a year to date basis has increased 3.7% when compared to the same period last year.  Our property book has changed significantly with greater diversity and reduced loss activity.

Investment Performance

Net investment income for the quarter was $70.5 million compared with $78.8 million in the second quarter of 2007, due primarily to the performance of our fund of hedge funds and a slight reduction in book yield. This was a significant improvement on the first quarter of 2008 as a result of the positive contribution from the funds of hedge funds. Funds of hedge funds contributed $10.8 million in the quarter against the backdrop of volatile market conditions. Net investment income year to date was $109.6 million compared with $146.3 million in the first half of 2007 with the decrease attributable mainly to the reduced contribution from our investments in funds of hedge funds. The quarter also included $88.6 million of net unrealized investment losses on the fixed term bond portfolio. The book yield on the fixed income element of our portfolio has remained stable at 4.8% when compared to the end of the first quarter of 2008, and decreased marginally when compared with 4.9% at the end of the second quarter in 2007. The average credit quality of our fixed income book is AA+, with 89% of the portfolio being graded A or higher.

Capital Management

On May 13, 2008, Aspen repurchased $100 million of ordinary shares representing approximately 4% of Aspen’s market capitalization at that date. The share repurchase of $100 million was funded from cash on hand of the Company.

Outlook for 2008

The Company expects that for the remainder of 2008 pricing will continue to soften in most lines. Total gross written premium levels will remain within the original guidance of $1.8 billion +/- 5%. Volatility in the capital and equity markets is expected to continue throughout the remainder of the year and as a result guidance for investment income has been revised to a range of $230 million to $265 million, with fixed income and short-term investments expected to contribute $230 million to $245 million and funds of hedge funds are expected to

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contribute less than $20 million. The assumed cat load has also been revised to $115 million for the full year reflecting experience of the half year. Estimated return on average equity is unchanged in the range of 13.0% to 16.0% for 2008, assuming normal loss experience for the remainder of the year.

Earnings conference call

Aspen will hold a conference call to discuss its financial results on Thursday, July 31, 2008 at 8:30 a.m. (Eastern Time).

CONFERENCE CALL PARTICIPATION DETAILS – July 31, 2008 at 8:30 a.m. (EST)

Participant Dial-In Numbers:	+1 (888) 459-5609 (US Toll Free)
	+1 (404) 665-9920 (International)
Conference ID:	51488921

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.

REPLAY DETAILS

A replay of the call will be available for 10 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:	51488921

Investor Contact:
Aspen Insurance Holdings Limited
Tania Kerno, Head of Communications	T: +44 (0) 20 7184 8855
Noah Fields, Head of Investor Relations	T: +1 441-297-9382
European Press Contact:
Citigate Dewe Rogerson
Justin Griffiths	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
(Unaudited)

(in US$ millions except for per share data)	As at June 30, 2008		As at December 31, 2007
ASSETS
Total investments		$5,361.6		$5,227.3
Cash and cash equivalents		620.8		651.4
Reinsurance recoverables		330.6		381.7
Premiums receivables		792.0		575.6
Other assets		394.1		365.3
Total assets		$7,499.1		$7,201.3
LIABILITIES
Losses and loss adjustment expenses		$2,944.4		$2,946.0
Unearned premiums		1,018.9		757.6
Other payables		432.4		430.6
Long-term debt		249.5		249.5
Total liabilities		$4,645.2		$4,383.7
SHAREHOLDERS’ EQUITY
Total shareholders’ equity		2,853.9		2,817.6
Total liabilities and shareholders’ equity		$7,499.1		$7,201.3
Book value per share		$29.84		$27.95
Diluted book value per share (treasury stock method)		$28.99		$27.08

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Aspen Insurance Holdings Limited
Summary Consolidated Statements of Income
(Unaudited)

	Three Months Ended			Three Months Ended
(in US$ millions except for percentages)	June 30, 2008			June 30, 2007
UNDERWRITING REVENUES
Gross written premiums		$528.8			$503.5
Premiums ceded		(22.8	)		(85.0	)
Net written premiums		506.0			418.5
Change in unearned premiums		(108.7	)		32.7
Net earned premiums		397.3			451.2
UNDERWRITING EXPENSES
Losses and loss expenses		188.3			272.7
Acquisition expenses		65.0			81.7
General and administrative expenses		57.1			44.4
Total underwriting expenses		310.4			398.8
Underwriting income		86.9			52.4
OTHER OPERATING REVENUE
Net investment income		70.5			78.8
Interest expense		(4.0	)		(4.4	)
Total other operating revenue		66.5			74.4
Other income		—			1.9
OPERATING INCOME BEFORE TAX		153.4			128.7
OTHER
Net realized and unrealized exchange gains (losses)		(5.0	)		8.0
Net realized and unrealized investment gains (losses)		0.8			(5.6	)
INCOME BEFORE TAX		149.2			131.1
Income taxes expense		(22.3	)		(16.4	)
NET INCOME AFTER TAX		126.9			114.7
Dividends paid on ordinary shares		(12.8	)		(13.2	)
Dividends paid on preference shares		(7.0	)		(7.0	)
Retained income		$107.1			$94.5
Components of net income (after tax)
Operating income		$131.2			$110.8
Net realized and unrealized exchange gains (losses) (after tax)		(5.0	)		8.0
Net realized and unrealized investment gains (losses) (after tax)		0.7			(4.1	)
NET INCOME AFTER TAX		$126.9			$114.7
Loss ratio		47.4	%		60.5	%
Policy acquistion expense ratio		16.4	%		18.1	%
General and administrative expense ratio		14.4	%		9.8	%
Expense ratio		30.8	%		27.9	%
Combined ratio		78.2	%		88.4	%

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Aspen Insurance Holdings Limited
Summary Consolidated Financial Data
(Unaudited)

	Three Months Ended				Six Months Ended
	June 30,		June 30,		June 30,		June 30,
(in US$ except for number of shares)	2008		2007		2008		2007
Basic earnings per ordinary share
Net income adjusted for preference share dividend		$1.44		$1.22		$2.31		$2.53
Operating income adjusted for preference dividend		$1.49		$1.18		$2.30		$2.47
Diluted earnings per ordinary share
Net income adjusted for preference share dividend		$1.39		$1.19		$2.24		$2.46
Operating income adjusted for preference dividend		$1.44		$1.14		$2.23		$2.40
Weighted average number of ordinary shares outstanding (in millions)		83.513		88.205		84.512		88.014
Weighted average number of ordinary shares outstanding and dilutive potential ordinary shares (in millions)		86.010		90.827		86.980		90.634
Book value per ordinary share						$29.84		$24.44
Diluted book value (treasury stock method)						$28.99		$23.63
Ordinary shares outstanding at end of the period (in millions)						81.321		88.545
Ordinary shares outstanding and dilutive potential ordinary shares at end of the period (treasury stock method) (in millions)						83.691		91.553

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Aspen Insurance Holdings Limited
Summary Consolidated Segment Information
(Unaudited)

	Three Months Ended			Three Months Ended
(in US$ millions except for percentages)	June 30, 2008			June 30, 2007
Gross written premiums
Property Reinsurance		$170.5			$190.3
Casualty Reinsurance		56.8			79.4
International Insurance		258.9			198.9
U.S. Insurance		42.6			34.9
Total		$528.8			$503.5
Premiums ceded
Property Reinsurance		$5.0			$74.7
Casualty Reinsurance		2.3			1.3
International Insurance		7.3			2.0
U.S. Insurance		8.2			7.0
Total		$22.8			$85.0
Net written premiums
Property Reinsurance		$165.5			$115.6
Casualty Reinsurance		54.5			78.1
International Insurance		251.6			196.9
U.S. Insurance		34.4			27.9
Total		$506.0			$418.5
Net earned premiums
Property Reinsurance		$123.6			$144.3
Casualty Reinsurance		85.8			125.7
International Insurance		162.9			156.0
U.S. Insurance		25.0			25.2
Total		$397.3			$451.2
Underwriting profit
Property Reinsurance		$43.3			$32.7
Casualty Reinsurance		7.3			6.7
International Insurance		34.1			18.7
U.S. Insurance		2.2			(5.7	)
Total		$86.9			$52.4
Combined ratio
Property Reinsurance		65.0	%		77.3	%
Casualty Reinsurance		91.5	%		94.7	%
International Insurance		79.2	%		88.0	%
U.S. Insurance		91.0	%		122.6	%
Total		78.2	%		88.4	%

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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, the United States, the United Kingdom, Singapore and Switzerland. For the six months ended June 30, 2008, Aspen reported gross written premiums of $1,125.0 million, net income of $208.1 million and total assets of $7.5 billion. 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 impact of deteriorating credit environment created by the sub-prime crisis and global credit crunch; a decline in the value of our investment portfolio or a rating downgrade of the securities in our portfolio; Aspen’s reliance on loss reports received from cedants and loss adjustors; Aspen’s reliance on industry loss estimates and those generated by modeling techniques; any changes in Aspen’s reinsurers’ credit quality; changes in assumptions on flood damage exclusions as a result of prevailing lawsuits and case law; the amount and timing of reinsurance recoverables and reimbursements actually received by Aspen from its reinsurers; the impact that our future operating results, capital position and rating agency and other considerations have on the execution of any capital management initiatives; 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; the impact of any capital management activities on our financial condition; 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 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 Aspen’s loss limitation methods; changes in the availability, cost or quality of reinsurance or retrocessional coverage, which may affect our decision to purchase such 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, A.M. Best Company or Moody’s Investors Service; 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 2008 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; decreased demand for Aspen’s insurance or reinsurance products and cyclical downturn of the industry; changes in governmental regulations, interpretations or tax laws in jurisdictions where Aspen conducts business; proposed and future changes to insurance laws and regulations, including with respect to U.S. state- and other government-sponsored reinsurance funds and primary insurers; 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 29, 2008. 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 Equity (“Operating ROE”) is a non-GAAP financial measure which divides operating income by average equity. Annualized Operating Return on 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 28 of Aspen’s financial supplement for a reconciliation of operating income to net income and page 7 for a reconciliation of average equity. Aspen’s financial supplement can be obtained from the Investor Relations section of Aspen’s website at www.aspen.bm.

(2) 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 28 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.

(3) 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 June 30, 2008

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

AHL: NYSE

www.aspen.bm

Investor Contact:

Aspen Insurance Holdings Limited

Tania Kerno, Head of Communications

email: tania.kerno@aspen-re.com

T: +44 (0) 20 7184 8855

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
Financial Highlights		2
Consolidated Statements of Operations — Quarterly		3
Consolidated Statements of Operations — Year to Date		4
Consolidated Balance Sheets		5
Earnings Per Share and Book Value Per Share		6
Return on Average Equity		7
Consolidated Underwriting Results By Operating Segment		8-9
Operating Segment — Quarterly Results		10-13
Gross Written Premiums by Segment and Line of Business		14
Accident Year Loss Ratios		15-16
Consolidated Statements of Changes In Shareholders’ Equity		17
Consolidated Statements of Comprehensive Income		18
Consolidated Statements of Cash Flows		19
Reserves For Losses and Loss Expenses		20
Reserves By Operating Segment		21
Prior Year Reserve Releases		22
Ratings Of Reinsurers		23
Consolidated Investment Portfolio		24
Investment Analysis		25
Book Value Per Ordinary Share		26
Diluted Share Analysis		27
Operating Income Reconciliation		28
Net 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, 2007. Unless otherwise noted, all data is in US dollars millions, except for per share, percentage and ratio information.

In presenting the Company’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 the Company’s results of operations in a manner that allows for a more complete understanding of the underlying trends in the Company’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 the Company 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.

The Company 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. The Company 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, the Company believes that showing operating income enables investors, analysts, rating agencies and other users of its financial information to more easily analyze the Company’s results of operations in a manner similar to how management analyzes the Company’s underlying business performance. Operating income should not be viewed as a substitute for GAAP net income. Please see page 28 for a reconciliation of operating income to net income.

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

The Company 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, the Company 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 the Company’s results of operations in a manner similar to how management analyzes the Company’s underlying business performance. Net income excluding net income or losses for other investments accounted for by the equity method should not be viewed as a substitute for GAAP net income. Please see page 29 for a reconciliation of net income excluding net income or losses for other investments accounted for by the equity method income to net income.

Annualized Operating Return on Average Equity (“Operating ROAE”) (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 the Company 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.

The Company presents Operating ROAE 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 28 for a reconciliation of operating income to net income and page 7 for a reconciliation of average equity.

Diluted book value per ordinary share (a non-GAAP financial measure): The Company has included diluted book value per ordinary share because it takes into account the effect of dilutive securities; therefore, the Company believes it is a better measure of calculating shareholder returns than book value per share. Please see page 26 for a reconciliation of diluted book value per share to basic book value per share.

Underwriting ratios (GAAP financial measures): The Company, 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 US 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 pages 15 and 16 for a reconciliation of accident year loss ratios to loss ratios calculated in accordance with U.S. GAAP.

1

Aspen Insurance Holdings Limited
Financial Highlights

	Three Months Ended June 30									Six Months Ended June 30
(in US$ millions except for percentages, share and per share amounts)	2008			2007			Change			2008			2007			Change
Gross written premium	$	528.8		$	503.5			5.0	%	$	1,125.0		$	1,140.0			(1.3%)
Net written premium	$	506.0		$	418.5			20.9	%	$	1,025.6		$	973.6			5.3%
Net earned premium	$	397.3		$	451.2			(11.9	%)	$	788.9		$	890.2			(11.4%)
Net income after tax	$	126.9		$	114.7			10.6	%	$	208.1		$	236.6			(12.1%)
Operating income after tax	$	131.2		$	110.8			18.4	%	$	207.2		$	231.4			(10.5%)
Earnings Per Share and Book Value Per Share
Basic earnings per ordinary share
Net income adjusted for preference share dividend	$	1.44		$	1.22			18.0	%	$	2.31		$	2.53			(8.7%)
Operating income adjusted for preference share dividend	$	1.49		$	1.18			26.3	%	$	2.30		$	2.47			(6.9%)
Diluted earnings per ordinary share
Net income adjusted for preference share dividend	$	1.39		$	1.19			16.8	%	$	2.24		$	2.46			(8.9%)
Operating income adjusted for preference share dividend	$	1.44		$	1.14			26.3	%	$	2.23		$	2.40			(7.1%)
Book value per ordinary share	$	29.84		$	24.44			22.1	%	$	29.84		$	24.44			22.1%
Diluted book value per ordinary share (treasury stock method)	$	28.99		$	23.63			22.7	%	$	28.99		$	23.63			22.7%
Weighted average number of ordinary shares outstanding (in millions of shares)		83.513			88.205			(5.3	%)		84.512			88.014			(4.0%)
Diluted weighted average number of ordinary shares outstanding (in millions of shares)		86.010			90.827			(5.3	%)		86.980			90.634			(4.0%)
Underwriting Ratios
Loss ratio		47.4	%		60.5	%					50.1	%		55.9	%
Policy acquisition cost ratio		16.4	%		18.1	%					17.9	%		17.9	%
General and administrative expense ratio		14.4	%		9.8	%					13.7	%		10.1	%
Expense ratio		30.8	%		27.9	%					31.6	%		28.0	%
Combined ratio		78.2	%		88.4	%					81.7	%		83.9	%
Return On Equity
Average equity (1)	$	2,356.1		$	2,109.0					$	2,335.2		$	2,057.0
Return on average equity
Net income adjusted for preference share dividend		5.1	%		5.1	%					8.3	%		10.8	%
Operating income adjusted for preference share dividend		5.3	%		4.9	%					8.3	%		10.6	%
Annualized Return on Average Equity
Net income		20.4	%		20.4	%					16.6	%		21.7	%
Operating income		21.2	%		19.7	%					16.6	%		21.1	%

See pages 7, 26, 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.

2

Aspen Insurance Holdings Limited

Consolidated Statements Of Operations — Quarterly

(in US$ millions except for percentages)	Q2 2008			Q1 2008			Q4 2007			Q3 2007			Q2 2007			Q2 2006
UNDERWRITING REVENUES
Gross written premiums		528.8			$596.2			$305.0			$373.5			$503.5			$522.4
Premiums ceded		(22.8	)		(76.6	)		(26.0	)		(24.7	)		(85.0	)		(22.3	)
Net written premiums		506.0			519.6			279.0			348.8			418.5			500.1
Change in unearned premiums		(108.7	)		(128.0	)		144.7			70.9			32.7			(71.1	)
Net earned premiums		397.3			391.6			423.7			419.7			451.2			429.0
UNDERWRITING EXPENSES
Losses and loss expenses		188.3			207.2			201.7			219.9			272.7			223.8
Acquisition expenses		65.0			76.4			78.4			76.1			81.7			83.2
General and administrative expenses		57.1			50.8			56.5			58.6			44.4			43.0
Total underwriting expenses		310.4			334.4			336.6			354.6			398.8			350.0
Underwriting income		86.9			57.2			87.1			65.1			52.4			79.0
OTHER OPERATING REVENUE
Net investment income		70.5			39.1			80.3			72.4			78.8			49.9
Interest expense		(4.0	)		(3.9	)		(2.9	)		(4.2	)		(4.4	)		(4.0	)
Total other operating revenue		66.5			35.2			77.4			68.2			74.4			45.9
Other income (expense)		—			(2.2	)		(3.8	)		(2.7	)		1.9			(0.6	)
OPERATING INCOME BEFORE TAX		153.4			90.2			160.7			130.6			128.7			124.3
OTHER
Net realized and unrealized exchange gains (losses)		(5.0	)		4.3			(2.1	)		9.2			8.0			6.6
Net realized and unrealized investment gains (losses)		0.8			1.0			(0.8	)		(1.9	)		(5.6	)		(3.7	)
INCOME BEFORE TAX		149.2			95.5			157.8			137.9			131.1			127.2
Income taxes expense		(22.3	)		(14.3	)		(22.6	)		(20.7	)		(16.4	)		(25.4	)
NET INCOME AFTER TAX		126.9			81.2			135.2			117.2			114.7			101.8
Dividends paid on ordinary shares		(12.8	)		(12.9	)		(13.3	)		(13.3	)		(13.2	)		(14.3	)
Dividend paid on preference shares		(7.0	)		(6.9	)		(6.9	)		(6.9	)		(7.0	)		(3.2	)
Retained income		$107.1			$61.4			$115.0			$97.0			$94.5			$84.3
Components of net income (after tax)					.
Operating income		$131.2			$76.0			$138.0			$109.2			$110.8			$98.3
Net realized and unrealized exchange gains (losses) (after tax)		(5.0	)		4.3			(2.1	)		9.2			8.0			6.6
Net realized and unrealized investment gains (losses) (after tax)		0.7			0.9			(0.7	)		(1.2	)		(4.1	)		(3.1	)
NET INCOME AFTER TAX		$126.9			$81.2			$135.2			$117.2			$114.7			$101.8
Loss ratio		47.4%			52.9%			47.6%			52.4%			60.5%			52.2%
Policy acquisition expense ratio		16.4%			19.5%			18.5%			18.1%			18.1%			19.4%
General and administrative expense ratio		14.4%			13.0%			13.3%			14.0%			9.8%			10.0%
Expense ratio		30.8%			32.5%			31.8%			32.1%			27.9%			29.4%
Combined ratio		78.2%			85.4%			79.4%			84.5%			88.4%			81.6%
Basic Earnings Per Share		$1.44			$0.87			$1.48			$1.24			$1.22			$1.04
Diluted Earnings Per Share		$1.39			$0.85			$1.44			$1.21			$1.19			$1.01
Annualized Return on Average Equity
Net income		20.4%			12.8%			22.8%			20.2%			20.4%			20.4%
Operating income		21.2%			12.0%			23.2%			18.7%			19.7%			19.6%

See pages 7, 26, 27, 28 and 29 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures.

3

Aspen Insurance Holdings Limited

Consolidated Statements of Operations — Year To Date

	Six Months Ended June 30
(in US$ millions except for percentages)	2008			2007			2006
UNDERWRITING REVENUES
Gross written premiums	$	1,125.0		$	1,140.0		$	1,201.1
Premiums ceded		(99.4	)		(166.4	)		(249.1	)
Net written premiums		1,025.6			973.6			952.0
Change in unearned premiums		(236.7	)		(83.4	)		(120.4	)
Net earned premiums		788.9			890.2			831.6
UNDERWRITING EXPENSES
Losses and loss expenses		395.5			498.2			456.2
Acquisition expenses		141.4			159.4			176.5
General and administrative expenses		107.9			89.7			81.2
Total underwriting expenses		644.8			747.3			713.9
Underwriting income		144.1			142.9			117.7
OTHER OPERATING REVENUE
Net investment income		109.6			146.3			94.4
Interest expense		(7.9	)		(8.6	)		(7.9	)
Total other operating revenue		101.7			137.7			86.5
Other income (expense)		(2.2	)		(5.4	)		(2.5	)
OPERATING INCOME BEFORE TAX		243.6			275.2			201.7
OTHER
Net realized and unrealized exchange gains (losses)		(0.7	)		13.5			7.9
Net realized and unrealized investment gains (losses)		1.8			(10.4	)		(5.1	)
INCOME BEFORE TAX		244.7			278.3			204.5
Income taxes		(36.6	)		(41.7	)		(40.9	)
NET INCOME AFTER TAX		208.1			236.6			163.6
Dividends paid on ordinary shares		(25.7	)		(26.4	)		(28.6	)
Dividends paid on preference shares		(13.9	)		(13.9	)		(7.1	)
Retained income	$	168.5		$	196.3		$	127.9
Components of net income (after tax)
Operating income	$	207.2		$	231.4		$	160.0
Net realized and unrealized exchange gains (losses) (after tax)		(0.7	)		13.5			7.9
Net realized and unrealized investment gains (losses) (after tax)		1.6			(8.3	)		(4.3	)
NET INCOME AFTER TAX	$	208.1		$	236.6		$	163.6
Loss ratio		50.1%			55.9%			54.8%
Policy acquisition expense ratio		17.9%			17.9%			21.2%
General and administrative expense ratio		13.7%			10.1%			9.8%
Expense ratio		31.6%			28.0%			31.0%
Combined ratio		81.7%			83.9%			85.8%

See pages 7, 26, 27, 28 and 29 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures.

4

Aspen Insurance Holdings Limited
Consolidated Balance Sheets

	Jun-30		Mar-31		Dec-31		Sep-30		Jun-30
(in US$ millions except for per share amounts)	2008		2008		2007		2007		2007
ASSETS
Investments
Fixed maturities	$	4,612.7	$	4,472.2	$	4,385.8	$	4,176.4	$	4,083.9
Other investments		555.3		544.5		561.4		489.5		481.6
Short-term investments		193.6		309.3		280.1		553.3		492.1
Total investments		5,361.6		5,326.0		5,227.3		5,219.2		5,057.6
Cash and cash equivalents		620.8		695.7		651.4		567.2		397.9
Reinsurance recoverables
Unpaid losses		231.7		276.0		304.7		315.8		324.4
Ceded unearned premiums		98.9		121.8		77.0		102.1		130.2
Receivables
Underwriting premiums		792.0		716.2		575.6		718.8		810.0
Other		79.0		50.3		59.8		84.8		48.8
Funds Withheld		76.9		100.0		104.5		99.2		94.0
Deferred policy acquisition costs		167.4		151.6		133.9		152.9		166.3
Derivatives at fair value		11.3		15.4		17.3		19.2		27.2
Office properties and equipment		30.4		28.0		27.8		25.1		24.9
Other assets		20.9		17.7		13.8		13.6		13.3
Intangible assets		8.2		8.2		8.2		8.2		8.2
Total assets	$	7,499.1	$	7,506.9	$	7,201.3	$	7,326.1	$	7,102.8
LIABILITIES
Insurance reserves
Losses and loss adjustment expenses	$	2,944.4	$	2,950.3	$	2,946.0	$	2,963.0	$	2,854.5
Unearned premiums		1,018.9		930.1		757.6		931.7		1,028.8
Total insurance reserves		3,963.3		3,880.4		3,703.6		3,894.7		3,883.3
Payables
Reinsurance premiums		115.6		133.1		81.3		89.1		132.2
Taxation		82.6		114.3		120.2		109.9		90.2
Accrued expenses and other payables		219.7		189.6		210.1		229.0		134.3
Liabilities under derivative contracts		14.5		17.3		19.0		20.7		22.4
Total payables		432.4		454.3		430.6		448.7		379.1
Long-term debt		249.5		249.5		249.5		249.5		249.4
Total liabilities		4,645.2		4,584.2		4,383.7		4,592.9		4,511.8
SHAREHOLDERS’ EQUITY
Ordinary shares		0.1		0.1		0.1		0.1		0.1
Preference shares		—		—		—		—		—
Additional paid-in capital		1,753.3		1,849.5		1,846.1		1,890.5		1,933.8
Retained earnings		1,027.3		920.2		858.8		743.8		646.8
Accumulated other comprehensive income, net of taxes		73.2		152.9		112.6		98.8		10.3
Total shareholders’ equity		2,853.9		2,922.7		2,817.6		2,733.2		2,591.0
Total liabilities and shareholders’ equity	$	7,499.1	$	7,506.9	$	7,201.3	$	7,326.1	$	7,102.8
Book Value Per Ordinary Share	$	29.84	$	29.22	$	27.95	$	26.46	$	24.44

See pages 7, 26, 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

Earnings Per Share and Book Value Per Share

	Three Months Ended				Six Months Ended
	June 30,		June 30,		June 30,		June 30,
(in US$ except for number of shares)	2008		2007		2008		2007
Basic earnings per ordinary share
Net income adjusted for preference share dividend		$1.44		$1.22		$2.31		$2.53
Operating income adjusted for preference dividend		$1.49		$1.18		$2.30		$2.47
Diluted earnings per ordinary share
Net income adjusted for preference share dividend		$1.39		$1.19		$2.24		$2.46
Operating income adjusted for preference dividend		$1.44		$1.14		$2.23		$2.40
Weighted average number of ordinary shares outstanding (in millions)		83.513		88.205		84.512		88.014
Weighted average number of ordinary shares outstanding and dilutive potential ordinary shares (in millions)		86.010		90.827		86.980		90.634
Book value per ordinary share						$29.84		$24.44
Diluted book value (treasury stock method)						$28.99		$23.63
Ordinary shares outstanding at end of the period (in millions)						81.321		88.545
Ordinary shares outstanding and dilutive potential ordinary shares at end of the period (treasury stock method) (in millions)						83.691		91.553

See pages 7, 26, 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

Return On Average Equity

	Three Months Ended						Six Months Ended
(in US$ millions except for percentages)	June 30, 2008			June 30, 2007			June 30, 2008			June 30, 2007
Closing shareholders’ equity	$	2,853.9			$2,591.0			$2,853.9			$2,591.0
Average adjustment		(497.8	)		(482.0	)		(518.7	)		(534.0	)
Average equity (1)	$	2,356.1			$2,109.0			$2,335.2			$2,057.0
Return on average equity for the quarter:
Net income adjusted for preference share dividend		5.1	%		5.1	%		8.3	%		10.8	%
Operating income adjusted for preference share dividend		5.3	%		4.9	%		8.3	%		10.6	%
Annualized Return on average equity
Net income		20.4	%		20.4	%		16.6	%		21.7	%
Operating income		21.2	%		19.7	%		16.6	%		21.1	%
Components of return on average equity
Return on average equity from underwriting activity (2)		3.7	%		2.5	%		6.2	%		6.9	%
Return on average equity from investment and other activity (3)		2.5	%		3.3	%		3.6	%		5.8	%
Pre-tax operating income return on average equity		6.2	%		5.8	%		9.8	%		12.7	%
Post-tax operating income return on average equity (4)		5.3	%		4.9	%		8.3	%		10.6	%

See pages 26, 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.

7

Aspen Insurance Holdings Limited

Consolidated Underwriting Results by Operating Segment

	Three Months Ended June 30, 2008										Three Months Ended June 30, 2007
	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		$170.5		$56.8		$258.9		$42.6		$528.8		$190.3		$79.4		$198.9		$34.9			$503.5
Net written premiums		165.5		54.5		251.6		34.4		506.0		115.6		78.1		196.9		27.9			418.5
Gross earned premiums		144.5		87.7		178.6		29.6		440.4		151.3		127.8		169.7		33.3			482.1
Net earned premiums		123.6		85.8		162.9		25.0		397.3		144.3		125.7		156.0		25.2			451.2
Losses and loss expenses		38.3		54.3		83.6		12.1		188.3		63.7		91.6		95.7		21.7			272.7
Policy acquisition expenses		23.6		11.7		26.0		3.7		65.0		31.1		17.2		28.3		5.1			81.7
Operating and administration expenses		18.4		12.5		19.2		7.0		57.1		16.8		10.2		13.3		4.1			44.4
Underwriting income (loss)		$43.3		$7.3		$34.1		$2.2		$86.9		$32.7		$6.7		$18.7		$(5.7	)		$52.4
Net reserves for loss and loss adjustment expenses		$396.0		$1,334.9		$906.6		$75.2		$2,712.7		$554.0		$1,107.1		$771.4		$97.6			$2,530.1
Ratios
Loss ratio		31.0%		63.3%		51.3%		48.4%		47.4%		44.1%		72.9%		61.3%		86.1%			60.5%
Policy acquisition expense ratio		19.1%		13.6%		16.1%		14.7%		16.4%		21.6%		13.7%		18.2%		20.2%			18.1%
Operating and administration expense ratio		14.9%		14.6%		11.8%		27.9%		14.4%		11.6%		8.1%		8.5%		16.3%			9.8%
Expense ratio		34.0%		28.2%		27.9%		42.6%		30.8%		33.2%		21.8%		26.7%		36.5%			27.9%
Combined ratio		65.0%		91.5%		79.2%		91.0%		78.2%		77.3%		94.7%		88.0%		122.6%			88.4%

8

Aspen Insurance Holdings Limited

Consolidated Underwriting Results by Operating Segment

	Six Months Ended June 30, 2008										Six Months Ended June 30, 2007
	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		$354.7		$238.9		$458.2		$73.2		$1,125.0		$382.4		$302.7		$384.2		$70.7			$1,140.0
Net written premiums		340.9		234.5		393.6		56.6		1,025.6		292.7		294.7		336.8		49.4			973.6
Gross earned premiums		284.8		183.4		343.9		55.6		867.7		312.6		238.8		332.5		72.2			956.1
Net earned premiums		250.6		180.5		313.1		44.7		788.9		297.7		232.1		302.8		57.6			890.2
Losses and loss expenses		76.3		115.8		181.3		22.1		395.5		127.8		152.4		177.0		41.0			498.2
Policy acquisition expenses		49.5		29.4		54.0		8.5		141.4		58.5		36.5		53.7		10.7			159.4
Operating and administration expenses		35.0		23.2		37.1		12.6		107.9		31.3		20.1		28.0		10.3			89.7
Underwriting income (loss)		$89.8		$12.1		$40.7		$1.5		$144.1		$80.1		$23.1		$44.1		$(4.4	)		$142.9
Net reserves for loss and loss adjustment expenses		$396.0		$1,334.9		$906.6		$75.2		$2,712.7		$554.0		$1,107.1		$771.4		$97.6			$2,530.1
Ratios
Loss ratio		30.4%		64.2%		57.9%		49.4%		50.1%		42.9%		65.7%		58.5%		71.2%			55.9%
Policy acquisition expense ratio		19.8%		16.3%		17.3%		19.0%		17.9%		19.7%		15.7%		17.7%		18.6%			17.9%
Operating and administration expense ratio		14.0%		12.9%		11.9%		28.2%		13.7%		10.4%		8.7%		9.3%		17.9%			10.1%
Expense ratio		33.8%		29.2%		29.2%		47.2%		31.6%		30.1%		24.4%		27.0%		36.5%			28.0%
Combined ratio		64.2%		93.4%		87.1%		96.6%		81.7%		73.0%		90.1%		85.5%		107.7%			83.9%

9

Aspen Insurance Holdings Limited

Property Reinsurance Segment — Quarterly Results

(in US$ millions except for percentages)	Q2 2008		Q1 2008		Q4 2007		Q3 2007		Q2 2007		Q1 2007		Q2 2006
Gross written premiums		$170.5		$184.2		$79.6		$139.5		$190.3		$192.1		$165.4
Net written premiums		165.5		175.4		70.8		131.5		115.6		177.1		34.2
Gross earned premiums		144.5		140.3		161.5		150.2		151.3		161.3		154.4
Net earned premiums		123.6		127.0		132.6		125.3		144.3		153.4		106.8
Net losses and loss expenses		38.3		38.0		50.0		42.9		63.7		64.1		47.7
Acquisition costs		23.6		25.9		33.5		25.4		31.1		27.4		35.2
Operating and administrative expenses		18.4		16.6		15.7		18.3		16.8		14.5		14.2
Total underwriting income		$43.3		$46.5		$33.4		$38.7		$32.7		$47.4		$9.7
Ratios
Loss ratio		31.0%		29.9%		37.7%		34.2%		44.1%		41.8%		44.7%
Policy acquisition expense ratio		19.1%		20.4%		25.3%		20.3%		21.6%		17.9%		33.0%
Operating and administrative expense ratio		14.9%		13.1%		11.8%		14.6%		11.6%		9.4%		13.2%
Expense ratio		34.0%		33.5%		37.1%		34.9%		33.2%		27.3%		46.2%
Combined ratio		65.0%		63.4%		74.8%		69.1%		77.3%		69.1%		90.9%

10

Aspen Insurance Holdings Limited

Casualty Reinsurance Segment — Quarterly Results

(in US$ millions except for percentages)	Q2 2008		Q1 2008		Q4 2007		Q3 2007			Q2 2007		Q1 2007		Q2 2006
Gross written premiums		$56.8		$182.1		$51.3		$77.5			$79.4		$223.3		$275.4
Net written premiums		54.5		180.0		53.3		77.1			78.1		216.6		265.6
Gross earned premiums		87.7		95.7		119.0		125.5			127.8		111.0		132.0
Net earned premiums		85.8		94.7		119.5		123.7			125.7		106.4		128.6
Losses and loss expenses		54.3		61.5		87.5		92.2			91.6		60.8		87.4
Policy acquisition expenses		11.7		17.7		13.3		19.8			17.2		19.3		25.9
Operating and administration expenses		12.5		10.7		14.0		13.8			10.2		9.9		10.1
Underwriting income (loss)		$7.3		$4.8		$4.7		$(2.1	)		$6.7		$16.4		$5.2
Ratios
Loss ratio		63.3%		64.9%		73.2%		74.5%			72.9%		57.2%		68.0%
Policy acquisition expense ratio		13.6%		18.7%		11.1%		16.0%			13.7%		18.1%		20.1%
Operating and administration expense ratio		14.6%		11.3%		11.8%		11.2%			8.1%		9.3%		7.9%
Expense ratio		28.2%		30.0%		22.9%		27.2%			21.8%		27.4%		28.0%
Combined ratio		91.5%		94.9%		96.1%		101.7%			94.7%		84.6%		96.0%

11

Aspen Insurance Holdings Limited

International Insurance Segment — Quarterly Results

(in US$ millions except for percentages)	Q2 2008		Q1 2008		Q4 2007		Q3 2007		Q2 2007		Q1 2007		Q2 2006
Gross written premiums		$258.9		$199.3		$149.8		$129.0		$198.9		$185.3		$197.5
Net written premiums		251.6		142.0		135.2		118.1		196.9		139.9		124.1
Gross earned premiums		178.6		165.3		162.2		164.2		169.7		162.8		169.5
Net earned premiums		162.9		150.2		147.7		146.7		156.0		146.8		138.6
Losses and loss expenses		83.6		97.7		56.6		75.3		95.7		81.3		80.8
Policy acquisition expenses		26.0		28.0		25.6		26.4		28.3		25.4		26.5
Operating and administration expenses		19.2		17.9		22.0		17.2		13.3		14.7		10.3
Underwriting income (loss)		$34.1		$6.6		$43.5		$27.8		$18.7		$25.4		$21.0
Ratios
Loss ratio		51.3%		65.0%		38.3%		51.3%		61.3%		55.4%		58.3%
Policy acquisition expense ratio		16.1%		18.6%		17.3%		18.0%		18.2%		17.3%		19.1%
Operating and administration expense ratio		11.8%		11.9%		14.9%		11.7%		8.5%		10.0%		7.4%
Expense ratio		27.9%		30.5%		32.2%		29.7%		26.7%		27.3%		26.5%
Combined ratio		79.2%		95.5%		70.5%		81.0%		88.0%		82.7%		84.8%

12

Aspen Insurance Holdings Limited

US Insurance Segment — Quarterly Results

(In US$ millions except for percentages)	Q2 2008		Q1 2008			Q4 2007		Q3 2007		Q2 2007			Q1 2007		Q2 2006
Gross written premiums		$42.6		$30.6			$24.3		$27.5		$34.9			$35.8		$40.4
Net written premiums		34.4		22.2			19.7		22.1		27.9			21.5		28.0
Gross earned premiums		29.6		26.0			31.4		33.2		33.3			38.9		37.6
Net earned premiums		25.0		19.7			23.9		24.0		25.2			32.4		28.6
Losses and loss expenses		12.1		10.0			7.6		9.5		21.7			19.3		16.5
Policy acquisition expenses		3.7		4.8			6.0		4.5		5.1			5.6		5.7
Operating and administration expenses		7.0		5.6			4.8		9.3		4.1			6.2		3.6
Underwriting income (loss)		$2.2		$(0.7	)		$5.5		$0.7		$(5.7	)		$1.3		$2.8
Ratios
Loss ratio		48.4%		50.8%			31.8%		39.6%		86.1%			59.6%		57.7%
Policy acquisition expense ratio		14.7%		24.3%			25.1%		18.8%		20.2%			17.3%		19.9%
Operating and administration expense ratio		27.9%		28.4%			20.1%		38.9%		16.3%			19.1%		12.6%
Expense ratio		42.6%		52.7%			45.2%		57.7%		36.5%			36.4%		32.5%
Combined ratio		91.0%		103.6%			77.0%		97.3%		122.6%			96.0%		90.2%

13

Aspen Insurance Holdings Limited

Gross Written Premiums By Segment And Line Of Business

(in US$ millions)	Q2 2008		Q1 2008		Q4 2007		Q3 2007		Q2 2007		Q1 2007		Q2 2006
Property Reinsurance
Treaty Catastrophe		$79.2		$111.6		$20.6		$60.1		$85.2		$118.6		$90.0
Treaty Risk Excess		40.0		29.9		9.0		35.7		66.6		23.0		39.5
Treaty Pro Rata		36.5		32.7		39.9		34.1		29.2		42.0		29.9
Property Facultative		14.8		10.0		10.1		9.6		9.3		8.5		6.0
		$170.5		$184.2		$79.6		$139.5		$190.3		$192.1		$165.4
Casualty Reinsurance
Treaty		$46.9		$89.6		$37.2		$53.5		$55.3		$131.3		$163.1
Non - US Treaty		5.7		89.5		11.6		20.5		22.2		88.4		105.8
Casualty Facultative		4.2		3.0		2.5		3.5		1.9		3.6		6.5
		$56.8		$182.1		$51.3		$77.5		$79.4		$223.3		$275.4
International Insurance
Marine and Specialty Liability		$47.4		$54.8		$30.0		$13.8		$40.1		$54.5		$47.1
Energy Property		41.7		23.4		8.1		21.3		45.0		28.2		15.1
Marine Hull		17.5		18.6		14.1		11.2		18.2		16.4		19.2
Aviation		23.1		11.2		42.2		23.7		26.6		10.8		30.6
U.K. Commercial Property		22.7		9.4		7.4		16.1		19.1		7.5		8.1
U.K. Commercial Liability		17.1		20.1		29.6		16.0		24.6		22.0		35.2
Non - Marine and Transportation Liability		14.3		7.1		7.1		—		—		—		—
Professional Liability		7.4		7.6		5.0		—		—		—		—
Excess Casualty		6.3		2.0		—		—		—		—		—
Financial Institutions		9.2		2.9		—		—		—		—		—
Political Risk		21.3		4.5		—		—		—		—		—
U.K. Commercial Property —Construction		4.5		—		—		—		—		—		—
Specialty Reinsurance		26.4		37.7		6.3		26.9		25.3		46.0		42.2
		$258.9		$199.3		$149.8		$129.0		$198.9		$185.4		$197.5
US Insurance
Property		$21.1		$10.5		$6.8		$7.9		$13.9		$12.4		$18.0
Casualty		21.5		20.1		17.5		19.6		21.0		23.3		22.4
		$42.6		$30.6		$24.3		$27.5		$34.9		$35.7		$40.4
Total Gross Written Premiums		$528.8		$596.2		$305.0		$373.5		$503.5		$636.5		$678.7

14

Aspen Insurance Holdings Limited

Accident Year Loss Ratios

	Three Months Ended June 30, 2008															Three Months Ended June 30, 2007
	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		31.0	%		63.3	%		51.3	%		48.4	%		47.4	%		44.1	%		72.9	%		61.3	%		86.1	%		60.5	%
Policy acquisition expense ratio		19.1	%		13.6	%		16.1	%		14.7	%		16.4	%		21.6	%		13.7	%		18.2	%		20.2	%		18.1	%
Operating and administration expense ratio		14.9	%		14.6	%		11.8	%		27.9	%		14.4	%		11.6	%		8.1	%		8.5	%		16.3	%		9.8	%
Expense ratio		34.0	%		28.2	%		27.9	%		42.6	%		30.8	%		33.0	%		21.8	%		26.7	%		36.5	%		27.9	%
Combined ratio		65.0	%		91.5	%		79.2	%		91.0	%		78.2	%		77.3	%		94.7	%		88.0	%		122.6	%		88.4	%
Accident Year Adjustment
Loss ratio		4.4	%		11.1	%		11.1	%		8.8	%		10.0	%		2.3	%		(2.4	)%		21.7	%		3.4	%		7.7	%
Policy acquisition expense ratio		(1.0	)%		0.2	%		(0.2	)%		0.6	%		(0.4	)%		(0.6	)%		(0.2	)%		0.2	%		2.3	%		(0.1	)%
Operating and administration expense ratio		0.1	%		(3.1	)%		0.9	%		4.4	%		(0.1	)%		0.1	%		1.2	%		1.2	%		(0.4	)%		0.8	%
Expense ratio		(0.9	)%		(2.9	)%		0.7	%		5.0	%		(0.5	)%		(0.5	)%		1.0	%		1.4	%		1.9	%		0.7	%
Combined ratio		3.5	%		8.2	%		11.8	%		13.8	%		9.5	%		1.8	%		(1.4	)%		23.1	%		5.3	%		8.4	%
Accident Year Ratios
Current Accident Year Loss Ratio		35.4	%		74.4	%		62.4	%		57.2	%		57.4	%		46.4	%		70.5	%		83.0	%		89.5	%		68.2	%
Policy acquisition expense ratio		18.1	%		13.8	%		15.9	%		15.3	%		16.0	%		21.0	%		13.5	%		18.4	%		22.5	%		18.0	%
Operating and administration expense ratio		15.0	%		11.5	%		12.7	%		32.3	%		14.3	%		11.7	%		9.3	%		9.7	%		15.9	%		10.6	%
Expense ratio		33.1	%		25.3	%		28.6	%		47.6	%		30.3	%		32.7	%		22.8	%		28.1	%		38.4	%		28.6	%
Combined ratio		68.5	%		99.7	%		91.0	%		104.8	%		87.7	%		79.1	%		93.3	%		111.1	%		127.9	%		96.8	%

15

Aspen Insurance Holdings Limited

Accident Year Loss Ratios

	Six Months Ended June 30, 2008															Six Months Ended June 30, 2007
	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		30.4	%		64.2	%		57.9	%		49.4	%		50.1	%		42.9	%		65.7	%		58.5	%		71.2	%		55.9	%
Policy acquisition expense ratio		19.8	%		16.3	%		17.3	%		19.0	%		17.9	%		19.7	%		15.7	%		17.7	%		18.6	%		17.9	%
Operating and administration expense ratio		14.0	%		12.9	%		11.9	%		28.2	%		13.7	%		10.4	%		8.7	%		9.3	%		17.9	%		10.1	%
Expense ratio		33.8	%		29.2	%		29.2	%		47.2	%		31.6	%		30.1	%		24.4	%		27.0	%		36.5	%		28.0	%
Combined ratio		64.2	%		93.4	%		87.1	%		96.6	%		81.7	%		73.0	%		90.1	%		85.5	%		107.7	%		83.9	%
Accident Year Adjustment
Loss ratio		8.1	%		9.6	%		8.5	%		16.6	%		10.0	%		(1.1	)%		6.1	%		15.3	%		0.6	%		6.7	%
Policy acquisition expense ratio		(0.7	)%		(0.4	)%		(0.1	)%		0.2	%		(0.3	)%		(0.4	)%		(0.2	)%		0.2	%		0.6	%		(0.1	)%
Operating and administration expense ratio		0.1	%		(2.0	)%		0.5	%		2.5	%		(0.1	)%		0.5	%		0.3	%		0.4	%		(0.8	)%		0.3	%
Expense ratio		(0.6	)%		(2.4	)%		0.4	%		2.7	%		(0.4	)%		0.1	%		0.1	%		0.6	%		(0.2	)%		0.2	%
Combined ratio		7.4	%		7.2	%		8.9	%		19.2	%		9.6	%		(1.0	)%		6.2	%		16.0	%		0.4	%		7.0	%
Accident Year Ratios
Current Accident Year Loss Ratio		38.5	%		73.8	%		66.4	%		66.0	%		60.1	%		41.8	%		71.8	%		73.8	%		71.8	%		62.6	%
Policy acquisition expense ratio		19.1	%		15.9	%		17.2	%		19.2	%		17.6	%		19.3	%		15.5	%		17.9	%		19.2	%		17.8	%
Operating and administration expense ratio		14.1	%		10.9	%		12.4	%		30.7	%		13.6	%		10.9	%		9.0	%		9.7	%		17.1	%		10.4	%
Expense ratio		33.2	%		26.8	%		29.6	%		49.9	%		31.2	%		30.2	%		24.5	%		27.6	%		36.3	%		28.2	%
Combined ratio		71.7	%		100.6	%		96.0	%		115.9	%		91.3	%		72.0	%		96.3	%		101.4	%		108.1	%		90.8	%

16

Aspen Insurance Holdings Limited

Consolidated Statements of Changes in Shareholders’ Equity

	Six Months Ended June 30
(in US$ millions)	2008			2007
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		1,846.1			1,921.7
New shares issued		—			7.1
Shares repurchased		(100.0	)		(0.1	)
Share-based compensation		7.2			5.1
End of period		1,753.3			1,933.8
Retained earnings
Beginning of period		858.8			450.5
Net income for the period		208.1			236.6
Dividends paid on ordinary and preference shares		(39.6	)		(40.3	)
End of period		1,027.3			646.8
Accumulated Other Comprehensive Income:
Cumulative foreign currency translation adjustments, net of taxes:
Beginning of period		80.2			59.1
Change for the period		14.2			26.7
End of period		94.4			85.8
Loss on derivatives
Beginning and end of period		(1.6	)		(1.8	)
Reclassification to interest payable		0.1			0.1
End of period		(1.5	)		(1.7	)
Unrealized appreciation (depreciation) on investments, net of taxes:
Beginning of period		34.0			(40.3	)
Change for the period		(53.7	)		(33.5	)
End of period		(19.7	)		(73.8	)
Total accumulated other comprehensive income		73.2			10.3
Total shareholders’ equity		$2,853.9			$2,591.0

17

Aspen Insurance Holdings Limited

Consolidated Statements of Comprehensive Income

	Six Months Ended June 30
(in US$ millions)	2008			2007
Net income		$208.1			$236.6
Other comprehensive income, net of taxes:
Reclassification adjustment for net realized (gains) losses included in net income		(3.8	)		3.0
Change in net unrealized gains and losses on available for sale securities held		(49.9	)		(36.5	)
Loss on derivatives reclassified to interest expense		0.1			0.1
Change in foreign currency translation adjustment		14.2			26.7
Other comprehensive loss		(39.4	)		(6.7	)
Comprehensive income		$168.7			$229.9

18

Aspen Insurance Holdings Limited

Condensed Consolidated Statements of Cash Flows

	Six Months Ended June 30
(in US$ millions)	2008			2007
Net cash from operating activities		$319.8			$319.5
Net cash used in investing activities		(193.2	)		(381.7	)
Net cash used in financing activities		(139.6	)		(33.2	)
Effect of exchange rate movements on cash and cash equivalents		(17.6	)		(1.7	)
Increase/(decrease) in cash and cash equivalents		(30.6	)		(97.1	)
Cash at beginning of the period		651.4			495.0
Cash at end of the period		$620.8			$397.9

19

Aspen Insurance Holdings Limited

Reserves For Losses And Loss Expenses

	June 30,			December 31,
(in US$ millions)	2008			2007
Provision for losses and loss expenses at start of period		$2,946.0			$2,820.0
Less reinsurance recoverable		(304.7	)		(468.3	)
Net loss and loss expenses at start of period		2,641.3			2,351.7
Loss reserve portfolio transfer		(15.5	)		11.0
Provision for losses and loss expenses for claims incurred:
Current period		475.5			1,027.2
Prior period release		(80.0	)		(107.4	)
Total incurred		395.5			919.8
Losses and loss expense payments for claims incurred		(324.3	)		(695.6	)
Foreign exchange (gains) losses		15.7			54.4
Net loss and loss expense reserves at end of period		2,712.7			2,641.3
Plus reinsurance recoverables on unpaid losses at end of period		231.7			304.7
Gross loss and loss expense reserves at end of period		$2,944.4			$2,946.0

20

Aspen Insurance Holdings Limited

Reserves By Operating Segment

	As at June 30, 2008							As at December 31, 2007
			Reinsurance							Reinsurance
(in US$ millions)	Gross		Recoverable			Net		Gross		Recoverable			Net
Property Reinsurance		$453.3		$(57.3	)		$396.0		$537.5		$(78.2	)		$459.3
Casualty Reinsurance		1,348.9		(14.0	)		1,334.9		1,276.3		(13.7	)		1,262.6
International Insurance		1,006.2		(99.6	)		906.6		999.2		(139.2	)		860.0
U.S. Insurance		136.0		(60.8	)		75.2		133.0		(73.6	)		59.4
Total losses and loss expense reserves		$2,944.4		$(231.7	)		$2,712.7		$2,946.0		$(304.7	)		$2,641.3

21

Aspen Insurance Holdings Limited

Prior Year Reserve Releases

	Six Months Ended June 30, 2008							Six Months Ended June 30, 2007
			Reinsurance								Reinsurance
(in US$ millions)	Gross		Recoverable			Net		Gross			Recoverable		Net
Property Reinsurance		$7.5		$8.7			$16.2		$(10.5	)		$1.7		$(8.8	)
Casualty Reinsurance		38.8		(0.5	)		38.3		13.0			4.4		17.4
International Insurance		17.5		0.6			18.1		25.5			10.3		35.8
U.S. Insurance		8.9		(1.5	)		7.4		(2.5	)		2.5		0.0
Release in reserves for prior years during the period		$72.7		$7.3			$80.0		$25.5			$18.9		$44.4

	Three Months Ended June 30, 2008							Three Months Ended June 30, 2007
			Reinsurance								Reinsurance
(in US$ millions)	Gross		Recoverable			Net		Gross			Recoverable		Net
Property Reinsurance		$3.4		$(0.8	)		$2.6		$(1.6	)		$0.6		$(1.0	)
Casualty Reinsurance		24.6		(0.6	)		24.0		(4.9	)		0.3		(4.6	)
International Insurance		12.5		(1.3	)		11.2		20.8			2.3		23.1
U.S. Insurance		2.6		0.1			2.7		(0.2	)		0.8		0.6
Release in reserves for prior years during the period		$43.1		$(2.6	)		$40.5		$14.1			$4.0		$18.1

22

Aspen Insurance Holdings Limited

Ratings Of Reinsurers

(in US$ millions except for percentages)	As at June 30, 2008				As at December 31, 2007
S&P
AAA		$23.0	9.9	%		$31.0	10.2	%
AA+		1.5	0.6	%		2.1	0.7	%
AA−		56.6	24.4	%		74.1	24.3	%
A+		90.2	38.9	%		118.3	38.8	%
A		1.7	0.7	%		1.7	0.6	%
A−		35.3	15.2	%		46.5	15.3	%
Fully collateralised		2.4	1.1	%		3.3	1.1	%
Not rated		21.0	9.2	%		27.7	9.0	%
		$231.7	100.0	%		$304.7	100.0	%
A.M. Best
A++		$23.0	9.9	%		$31.0	10.2	%
A+		36.6	15.8	%		46.3	15.2	%
A		126.6	54.6	%		166.9	54.8	%
A−		27.9	12.0	%		37.2	12.2	%
Fully collateralised		2.4	1.0	%		3.3	1.1	%
Not rated		15.2	6.7	%		20.0	6.5	%
		$231.7	100.0	%		$304.7	100.0	%

23

Aspen Insurance Holdings Limited

Consolidated Investment Portfolio

	As at June 30, 2008									Percentage of Total Fair Value
			Gross		Gross
	Amortized		Unrealized		Unrealized			Fair					March 31,			December 31,			December 31,
(in US$ millions except for percentages)	Cost		Gains		Losses			Value		June 30, 2008			2008			2007			2006
U.S. government		$665.1		$16.2		$(2.5	)		$678.8		11.3	%		12.0	%		10.9	%		19.4	%
U.S. government agency securities		329.8		5.7		(0.9	)		334.6		5.6	%		6.2	%		5.6	%		6.3	%
Corporate securities		1,639.8		7.0		(37.1	)		1,609.7		26.7	%		25.1	%		25.6	%		20.6	%
Foreign government		417.1		1.2		(8.4	)		409.9		6.8	%		6.8	%		7.2	%		8.5	%
Asset-backed securities		243.3		2.3		(0.7	)		244.9		4.1	%		3.5	%		3.8	%		5.6	%
Mortgage-backed securities		1,341.9		6.7		(13.8	)		1,334.8		22.2	%		20.1	%		20.8	%		12.9	%
Total fixed maturities		4,637.0		39.1		(63.4	)		4,612.7		76.7	%		73.7	%		73.9	%		73.3	%
Short-term investments		193.6		—		—			193.6		3.2	%		5.1	%		4.8	%		13.4	%
Total investments		$4,830.6		$39.1		$(63.4	)		$4,806.3		79.9	%		78.8	%		78.7	%		86.7	%
Other Investments									555.3		9.2	%		9.0	%		9.5	%		3.0	%
Cash									620.8		10.3	%		11.5	%		11.0	%		9.5	%
Accrued Interest									38.4		0.6	%		0.7	%		0.8	%		0.8	%
Total Investments									$6,020.8		100.0	%		100.0	%		100.0	%		100.0	%

24

Aspen Insurance Holdings Limited

Investment Analysis

(in US$ millions except for percentages)	Q2 2008			Q1 2008			Q4 2007			Q3 2007			Q2 2007			Q1 2007
Net investment income from fixed income investments		$59.7			$56.0			$68.4			$64.5			$64.0			$57.6
Net investment income (loss) from other investments		10.8			(16.9	)		11.9			7.9			14.8			9.9
Net investment income		70.5			39.1			80.3			72.4			78.8			67.5
Net realized investment gains (losses)		0.8			1.0			(0.8	)		(1.9	)		(5.6	)		(4.8	)
Change in unrealized gains (losses) on investments (gross of tax)		(110.4	)		44.4			65.0			68.1			(56.1	)		13.6
Total return on investments		$(39.1	)		$84.5			$144.5			$138.6			$17.1			$76.3
Portfolio Characteristics
Fixed income portfolio book yield		4.84	%		4.90	%		5.05	%		5.08	%		4.94	%		4.77	%
Fixed income portfolio duration		3.58 years			3.35 years			3.40 years			3.46 years			3.59 years			3.25 years

25

Aspen Insurance Holdings Limited

Book Value Per Ordinary Share

	Six Months Ended June 30
(in US$ except for number of shares)	2008			2007
Net Assets		$2,853.9			$2,591.0
Less: Intangible Assets		(8.2	)		(8.2	)
Preference Shares		(419.2	)		(419.2	)
Total		$2,426.5			$2,163.6
Ordinary Shares Outstanding (in millions)		81.321			88.545
Ordinary Shares and Dilutive Potential Ordinary Shares (in millions)		83.691			91.553
Book Value Per Ordinary Share		$29.84			$24.44
Diluted Book Value Per Ordinary Share (treasury stock method)		$28.99			$23.63

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

Diluted Share Analysis

	Three Months Ended June 30				Six Months Ended June 30
	2008		2007		2008		2007
Weighted average ordinary shares outstanding (millions)
Basic		83.513		88.205		84.512		88.014
Dilutive share equivalents:
Employee Options		1.113		1.578		1.235		1.535
Options issued to Appleby Trust (Bermuda) Limited		0.104		0.201		0.156		0.387
Performance Shares		1.047		0.598		0.848		0.471
Restricted share units		0.233		0.245		0.229		0.227
Weighted average diluted shares outstanding		86.010		90.827		86.980		90.634

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.

27

Aspen Insurance Holdings Limited

Operating Income Reconciliation

	Three Months Ended						Six Months Ended
	June 30,			June 30,			June 30,			June 30,
(in US$ millions except where stated)	2008			2007			2008			2007
Net income adjusted for preference share dividend		$119.9			$107.7			$194.2			$222.7
Add (deduct) after tax income:
Net exchange (gains) losses		5.0			(8.0	)		0.7			(13.5	)
Net realized (gains) losses on investments		(0.7	)		4.1			(1.6	)		8.3
Operating income adjusted for preference share dividend		124.2			103.8			193.3			217.5
Tax on operating income		22.2			17.9			36.4			43.8
Operating income before tax adjusted for preference share dividend		$146.4			$121.7			$229.7			$261.3
Weighted average ordinary shares outstanding (millions)
Basic		83.513			88.205			84.512			88.014
Dilutive share equivalents:					.
Employee Options		1.113			1.578			1.235			1.535
Options Issued To Appleby Trust (Bermuda) Limited (Names Trust)		0.104			0.201			0.156			0.387
Performance Shares		1.047			0.598			0.848			0.471
Restricted share units		0.233			0.245			0.229			0.227
Weighted average diluted shares outstanding		86.010			90.827			86.980			90.634
Basic per ordinary share data
Net income adjusted for preference share dividend		$1.44			$1.22			$2.31			$2.53
Add (deduct) after tax income
Net exchange (gains) losses		$0.06			$(0.09	)		$0.01			$(0.15	)
Net realized losses on investments		$(0.01	)		$0.05			$(0.02	)		$0.09
Operating income adjusted for preference shares dividend		$1.49			$1.18			$2.30			$2.47
Diluted per ordinary share data
Net income adjusted for preference share dividend		$1.39			$1.19			$2.24			$2.46
Add (deduct) after tax income
Net exchange (gains) losses		$0.06			$(0.10	)		$0.01			$(0.15	)
Net realized losses on investments		$(0.01	)		$0.05			$(0.02	)		$0.09
Operating income adjusted for preference share dividend		$1.44			$1.14			$2.23			$2.40

28

Aspen Insurance Holdings Limited

Net Income Reconciliation

	Three Months Ended						Six Months Ended
	June 30,			June 30,			June 30,			June 30,
(in US$ millions except where stated)	2008			2007			2008			2007
Net income adjusted for preference share dividend		$119.9			$107.7			$194.2			$222.7
Add (deduct) after tax income:
Other investments accounted for by the equity method (gains) losses		(10.8	)		(14.8	)		6.1			(24.7	)
Tax on other investments		1.6			2.2			(0.9	)		3.7
Net income adjusted for preference share dividend excluding net income or losses from other investments accounted for by the equity method		110.7			95.1			199.4			201.7
Weighted average ordinary shares outstanding (millions)
Basic		83.513			88.205			84.512			87.819
Dilutive share equivalents:					.
Employee Options		1.113			1.578			1.235			1.483
Options Issued To Appleby Trust (Bermuda) Limited (Names Trust)		0.104			0.201			0.156			0.619
Performance Shares		1.047			0.598			0.848			0.340
Restricted share units		0.233			0.245			0.229			0.227
Weighted average diluted shares outstanding		86.010			90.827			86.980			90.488
Basic per ordinary share data
Net income adjusted for preference share dividend		$1.44			$1.22			$2.31			$2.54
Add (deduct) after tax income
Other investments accounted for by the equity method (gains) losses		$(0.13	)		$(0.17	)		$0.07			$(0.28	)
Tax on other investments		$0.02			$0.02			$(0.01	)		$0.03
Net income adjusted for preference share dividend excluding net income or losses from other investments accounted for by the equity method		$1.33			$1.07			$2.37			$2.29
Diluted per ordinary share data
Net income adjusted for preference share dividend		$1.39			$1.19			$2.24			$2.46
Add (deduct) after tax income
Other investments accounted for by the equity method (gains) losses		$(0.13	)		$(0.16	)		$0.06			$(0.27	)
Tax on other investments		$0.02			$0.02			$(0.01	)		$0.04
Net income adjusted for preference share dividend excluding net income or losses from other investments accounted for by the equity method		$1.28			$1.05			$2.29			$2.23

29