Exhibit 99.1

HCC INSURANCE HOLDINGS REPORTS

RECORD FIRST QUARTER NET EARNINGS

AND EARNINGS PER SHARE

Highlights:

·Net earnings of $107.9 million, or $1.07 per diluted share

·GAAP combined ratio of 83.0%

·Gross written premium increased 4% to $746.7 million

·Net written premium increased 2% to $590.2 million

·Annualized return on equity of 11.6%

·Annualized operating return on equity(a) of 10.8%

·Book value per share increased 3% to $37.79

HOUSTON (April 29, 2014) . . .

HCC Insurance Holdings, Inc. (NYSE: HCC) today released results for its first quarter ended March 31, 2014.

Net earnings were $107.9 million, or $1.07 per diluted share, in the first quarter of 2014, compared to $105.9 million, or $1.05 per diluted share, in the same quarter of 2013.

The Company’s combined ratio was 83.0% for the first quarter of 2014, compared to 83.8% for the same quarter of 2013.  The net paid loss ratio was 63.1% and 53.4% for the respective periods.  HCC had no reserve development in either the first quarter of 2014 or 2013.  The 2014 and 2013 results included accident year pretax net catastrophe losses of $4.6 million and $5.2 million, respectively, which reduced net earnings by $0.03 per share in both quarters.

“We are pleased to begin 2014 with the best first quarter financial performance in HCC’s history.  Our businesses continue to deliver consistent, profitable results highlighted by a combined ratio of 83.0%,” said Christopher J.B. Williams, HCC’s Chief Executive Officer.

Gross written premium increased 4% to $746.7 million in the first quarter of 2014, compared to $720.2 million in the same quarter of 2013.  Net written premium increased 2% to $590.2 million versus $579.2 million in the respective quarters.  Net earned premium was $562.6 million in the first quarter of 2014, compared to $561.2 million in the same quarter of 2013.

Investment income increased to $56.8 million in the first quarter of 2014, compared to $55.8 million in the same quarter of 2013.  As of March 31, 2014, HCC’s fixed maturity securities portfolio had an average rating of AA, with a duration of 5.0 years and an average long-term tax equivalent yield of 4.4%.

HCC generated cash flow from operations of $95.5 million in the first quarter of 2014, compared to $2.1 million in the same quarter of 2013.  The Company’s cash flow was decreased by U.S. Surety collateral repayments of $6.1 million in 2014 and $67.1 million in 2013.  At March 31, 2014, the Company had $500.2 million of cash and short-term investments and $169.1 million of available capacity under its $600.0 million revolving loan facility.

The Company purchased 0.7 million shares of its common stock during the first quarter of 2014 for $31.4 million at an average cost of $42.66 per share.

As of March 31, 2014, total assets were $10.6 billion, shareholders’ equity was $3.8 billion and the Company’s debt to total capital ratio was 16.1%.

In the first quarter of 2014, HCC changed the presentation of certain lines of business within its existing segment reporting structure to further enhance the transparency of the Company’s segment results.  The reclassifications did not impact the individual segment results.  All prior data has been recast to be comparative with the 2014 presentation.

For further information about HCC’s 2014 first quarter earnings results, see the supplemental financial schedules that are available in the Investor Relations section of the Company’s website at http://ir.hcc.com.

HCC will hold an open conference call beginning at 8:00 a.m. Central Daylight Time on Wednesday, April 30.  To participate, the number for domestic calls is (800) 374-0290 and the number for international calls is (706) 634-0161.  There will also be a live webcast available on a listen-only basis that can be accessed through the Investor Relations section of the Company’s website at http://ir.hcc.com.  The webcast replay will be archived in the Investor Relations section of the HCC website through Friday, August 1, 2014.

Headquartered in Houston, Texas, HCC Insurance Holdings, Inc. is a leading specialty insurer with offices in the United States, the United Kingdom, Spain and Ireland.  HCC’s major domestic and international insurance companies have financial strength ratings of “AA (Very Strong)” from Standard & Poor’s Corporation, “A+ (Superior)” from A.M. Best Company, Inc., “AA (Very Strong)” from Fitch Ratings, and “A1 (Good Security)” from Moody’s Investors Service, Inc.

For more information about HCC, please visit http://www.hcc.com.

a)  Non-GAAP Financial Measure

Annualized operating return on equity is a non-GAAP financial measure under Regulation G and is calculated as net earnings excluding after-tax net realized investment gain/loss, other-than-temporary impairment credit losses, and foreign currency benefit/expense (collectively, operating earnings) divided by average shareholders’ equity excluding accumulated other comprehensive income.  To annualize a quarterly rate, the result is multiplied by four.  See the supplemental financial schedules for a reconciliation of this non-GAAP financial measure to corresponding GAAP amounts.  Management believes annualized operating return on equity is a useful measure for understanding the Company’s profitability relative to shareholders’

2

equity before consideration of investment-related gains/losses and foreign currency benefit/expense, both of which management excludes when evaluating operating results internally.

Contact:	Doug Busker, Director of Investor Relations
	HCC Insurance Holdings, Inc.
	Telephone:  (713) 996-1192

Forward-looking statements contained in this press release are made under “safe harbor” provisions of the Private Securities Litigation Reform Act of 1995 and involve a number of risks and uncertainties.  The types of risks and uncertainties which may affect the Company are set forth in its periodic reports filed with the Securities and Exchange Commission.

*     *     *     *     *

3

HCC Insurance Holdings, Inc. and Subsidiaries

Financial Highlights

(Unaudited, in thousands except per share data)

	Three months ended
	March 31,
	2014			2013
Gross written premium	$	746,722		$	720,205
Net written premium	590,182			579,184
Net earned premium	562,612			561,186
Net investment income	56,806			55,765
Total revenue	648,930			634,366
Net earnings	107,911			105,850
Operating earnings*	97,293			93,139
Earnings per share (diluted)	$	1.07		$	1.05
Weighted-average shares outstanding	98,913			99,287
Net loss ratio	57.2		%	59.3		%
Expense ratio	25.8		%	24.5		%
Combined ratio	83.0		%	83.8		%
Paid loss ratio	63.1		%	53.4		%

	March 31,			December 31,
	2014			2013
Total investments	$	6,949,415		$	6,718,692
Total assets	10,649,784			10,344,520
Shareholders’ equity	3,782,113			3,674,430
Debt to total capital ratio	16.1		%	15.1		%
Book value per share	$	37.79		$	36.62

*   Non-GAAP financial measure under Regulation G.  See calculation on S - 9.  Management believes operating earnings is a useful measure for understanding the Company’s profitability before consideration of investment-related gains/losses and foreign currency benefit/expense, both of which management excludes when evaluating operating results internally.

S-1

HCC Insurance Holdings, Inc. and Subsidiaries

Consolidated Balance Sheets

(Unaudited, in thousands)

	March 31,			December 31,
	2014			2013
ASSETS
Investments
Fixed maturity securities — available for sale, at fair value	$	6,095,626		$	6,022,473
Equity securities — available for sale, at fair value	426,089			517,466
Short-term investments	427,700			178,753
Total investments	6,949,415			6,718,692
Cash	72,524			58,301
Restricted cash and securities	122,950			125,777
Premium, claims and other receivables	630,844			580,107
Reinsurance recoverables	1,221,444			1,277,257
Ceded unearned premium	311,372			305,438
Ceded life and annuity benefits	55,599			56,491
Deferred policy acquisition costs	210,356			201,698
Goodwill	895,501			895,200
Other assets	179,779			125,559
Total assets	$	10,649,784		$	10,344,520
LIABILITIES
Loss and loss adjustment expense payable	$	3,847,417		$	3,902,132
Life and annuity policy benefits	55,599			56,491
Reinsurance, premium and claims payable	400,681			332,985
Unearned premium	1,167,308			1,134,849
Deferred ceding commissions	92,460			89,528
Notes payable	724,136			654,098
Accounts payable and accrued liabilities	580,070			500,007
Total liabilities	6,867,671			6,670,090
SHAREHOLDERS’ EQUITY
Common stock	126,062			125,577
Additional paid-in capital	1,082,735			1,073,105
Retained earnings	3,170,912			3,085,501
Accumulated other comprehensive income	162,221			118,651
Treasury stock	(759,817		)	(728,404		)
Total shareholders’ equity	3,782,113			3,674,430
Total liabilities and shareholders’ equity	$	10,649,784		$	10,344,520

S-2

HCC Insurance Holdings, Inc. and Subsidiaries

Consolidated Statements of Earnings

(Unaudited, in thousands except per share data)

	Three months ended
	March 31,
	2014			2013
REVENUE
Net earned premium	$	562,612		$	561,186
Net investment income	56,806			55,765
Other operating income	9,266			8,845
Net realized investment gain	20,246			8,570
Total revenue	648,930			634,366
EXPENSE
Loss and loss adjustment expense, net	321,844			332,697
Policy acquisition costs, net	69,041			66,949
Other operating expense	95,954			76,853
Interest expense	7,119			6,471
Total expense	493,958			482,970
Earnings before income tax expense	154,972			151,396
Income tax expense	47,061			45,546
Net earnings	$	107,911		$	105,850
Net earnings attributable to unvested stock	(1,692		)	(1,782		)
Net earnings available to common stock	$	106,219		$	104,068
Basic earnings per share data:
Net earnings per share	$	1.08		$	1.05
Weighted-average shares outstanding	98,662			99,056
Diluted earnings per share data:
Net earnings per share	$	1.07		$	1.05
Weighted-average shares outstanding	98,913			99,287
Cash dividends declared, per share	$	0.225		$	0.165

S-3

HCC Insurance Holdings, Inc. and Subsidiaries

Gross Written Premium

(Unaudited, in thousands)

	Three months ended March 31,
	2014		2013		Change
U.S. Property & Casualty
Aviation	$	32,447	$	36,998	(12	)%
Liability	43,472		37,093		17
Sports & Entertainment	42,142		34,435		22
Public Risk	20,723		21,441		(3	)
Other	34,223		45,170		(24	)
	173,007		175,137		(1	)
Professional Liability	105,428		104,019		1
Accident & Health
Medical Stop-loss	215,398		202,808		6
Other	20,519		12,753		61
	235,917		215,561		9
U.S. Surety & Credit
Surety	37,202		37,696		(1	)
Credit	13,850		14,553		(5	)
	51,052		52,249		(2	)
International
Marine & Energy	37,748		34,622		9
Property Treaty	67,992		72,345		(6	)
Surety & Credit	26,357		21,166		25
Liability	22,691		18,133		25
Other	26,239		21,541		22
	181,027		167,807		8
Exited Lines	291		5,432		nm
Totals	$	746,722	$	720,205	4	%

nm - Not meaningful

S-4

HCC Insurance Holdings, Inc. and Subsidiaries

Net Written Premium

(Unaudited, in thousands)

	Three months ended March 31,
	2014		2013		Change
U.S. Property & Casualty
Aviation	$	25,323	$	28,614	(12	)%
Liability	31,095		27,244		14
Sports & Entertainment	7,065		5,773		22
Public Risk	10,888		15,771		(31	)
Other	15,637		26,480		(41	)
	90,008		103,882		(13	)
Professional Liability	69,601		67,626		3
Accident & Health
Medical Stop-loss	214,232		202,594		6
Other	20,519		12,674		62
	234,751		215,268		9
U.S. Surety & Credit
Surety	32,816		33,690		(3	)
Credit	11,265		11,814		(5	)
	44,081		45,504		(3	)
International
Marine & Energy	24,885		21,473		16
Property Treaty	60,538		66,167		(9	)
Surety & Credit	23,047		18,649		24
Liability	21,144		16,570		28
Other	21,836		18,613		17
	151,450		141,472		7
Exited Lines	291		5,432		nm
Totals	$	590,182	$	579,184	2	%

nm - Not meaningful

S-5

HCC Insurance Holdings, Inc. and Subsidiaries

Net Earned Premium

(Unaudited, in thousands)

	Three months ended March 31,
	2014		2013		Change
U.S. Property & Casualty
Aviation	$	26,759	$	27,857	(4	)%
Liability	26,638		23,950		11
Sports & Entertainment	8,137		6,312		29
Public Risk	13,034		16,360		(20	)
Other	22,484		19,052		18
	97,052		93,531		4
Professional Liability	85,450		92,779		(8	)
Accident & Health
Medical Stop-loss	214,230		202,594		6
Other	17,913		14,531		23
	232,143		217,125		7
U.S. Surety & Credit
Surety	34,845		35,607		(2	)
Credit	12,098		11,570		5
	46,943		47,177		—
International
Marine & Energy	21,847		25,708		(15	)
Property Treaty	24,765		28,755		(14	)
Surety & Credit	19,936		18,213		9
Liability	19,136		17,175		11
Other	15,049		15,291		(2	)
	100,733		105,142		(4	)
Exited Lines	291		5,432		nm
Totals	$	562,612	$	561,186	—	%

nm - Not meaningful

S-6

HCC Insurance Holdings, Inc. and Subsidiaries

Net Investment Income and Unrealized Gain

(Unaudited, in thousands)

	Three months ended
	March 31,
	2014			2013
Sources of net investment income:
Fixed maturity securities
Taxable	$	23,260		$	25,960
Exempt from U.S. income taxes	28,583			27,889
Total fixed maturity securities	51,843			53,849
Equity securities	6,637			3,580
Other	431			(35		)
Total investment income	58,911			57,394
Investment expense	(2,105		)	(1,629		)
Net investment income	$	56,806		$	55,765
Unrealized gain on available for sale securities:
Increase (decrease) in unrealized gain for period, before tax	$	65,834		$	(38,965	)
Unrealized gain at:
March 31, 2014	$	219,898
December 31, 2013	$	154,064

S - 7

HCC Insurance Holdings, Inc. and Subsidiaries

Underwriting Ratios

(Unaudited)

	Three months ended
	March 31,
	2014		2013
U.S. Property & Casualty
Aviation	60.0	%	61.7	%
Liability	60.0		63.2
Sports & Entertainment	47.7		49.3
Public Risk	58.7		78.2
Other	13.7		20.6
Loss Ratio	48.1		55.8
Expense Ratio	28.3		27.1
Combined Ratio	76.4	%	82.9	%
Professional Liability
Loss Ratio	59.8	%	60.8	%
Expense Ratio	20.0		19.2
Combined Ratio	79.8	%	80.0	%
Accident & Health
Medical Stop-loss	74.9	%	75.2	%
Other	48.1		56.3
Loss Ratio	72.8		73.9
Expense Ratio	15.6		14.3
Combined Ratio	88.4	%	88.2	%
U.S. Surety & Credit
Surety	25.1	%	25.0	%
Credit	41.0		37.4
Loss Ratio	29.2		28.0
Expense Ratio	54.9		55.4
Combined Ratio	84.1	%	83.4	%
International
Marine & Energy	47.8	%	49.6	%
Property Treaty	20.9		24.3
Surety & Credit	48.6		63.5
Liability	51.3		49.9
Other	43.1		39.5
Loss Ratio	41.3		43.7
Expense Ratio	38.0		33.7
Combined Ratio	79.3	%	77.4	%
Consolidated
Loss Ratio	57.2	%	59.3	%
Expense Ratio	25.8		24.5
Combined Ratio	83.0	%	83.8	%

S - 8

HCC Insurance Holdings, Inc. and Subsidiaries

Reconciliation of Non-GAAP Financial Measures to GAAP

(Unaudited, in thousands)

	Three months ended
	March 31,
	2014			2013
Numerator:
GAAP net earnings	$	107,911		$	105,850
Exclude:
Net realized investment gain*	13,160			5,571
Foreign currency benefit (expense)*	(2,542		)	7,140
Total items excluded from operating earnings	10,618			12,711
Operating earnings	$	97,293		$	93,139
Denominator:
GAAP equity - beginning of period	$	3,674,430		$	3,542,612
Exclude - Accumulated other comprehensive income	118,651			295,271
Beginning equity, as adjusted	$	3,555,779		$	3,247,341
GAAP equity - end of period	$	3,782,113		$	3,585,249
Exclude - Accumulated other comprehensive income	162,221			268,100
Ending equity, as adjusted	$	3,619,892		$	3,317,149
Average equity, as adjusted	$	3,587,836		$	3,282,245
Annualized operating return on equity	10.8		%	11.4		%

* Net of tax, calculated using 35% statutory tax rate.

S - 9