-----BEGIN PRIVACY-ENHANCED MESSAGE-----
Proc-Type: 2001,MIC-CLEAR
Originator-Name: webmaster@www.sec.gov
Originator-Key-Asymmetric:
 MFgwCgYEVQgBAQICAf8DSgAwRwJAW2sNKK9AVtBzYZmr6aGjlWyK3XmZv3dTINen
 TWSM7vrzLADbmYQaionwg5sDW3P6oaM5D3tdezXMm7z1T+B+twIDAQAB
MIC-Info: RSA-MD5,RSA,
 Npn/Eh+ke+mbBNgdfBgiwW2Aa/9/sv0EdF/tUEViAT5dpVGQBR3qP8Q95yBwLmp8
 Okioa1918l8YyDLvhekILw==

<SEC-DOCUMENT>0001181431-08-057177.txt : 20081014
<SEC-HEADER>0001181431-08-057177.hdr.sgml : 20081013
<ACCEPTANCE-DATETIME>20081014161732
ACCESSION NUMBER:		0001181431-08-057177
CONFORMED SUBMISSION TYPE:	4/A
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20081008
FILED AS OF DATE:		20081014
DATE AS OF CHANGE:		20081014

ISSUER:		

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			HCC INSURANCE HOLDINGS INC/DE/
		CENTRAL INDEX KEY:			0000888919
		STANDARD INDUSTRIAL CLASSIFICATION:	FIRE, MARINE & CASUALTY INSURANCE [6331]
		IRS NUMBER:				760336636
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	BUSINESS ADDRESS:	
		STREET 1:		13403 NORTHWEST FRWY
		CITY:			HOUSTON
		STATE:			TX
		ZIP:			77040-6094
		BUSINESS PHONE:		7136907300

	MAIL ADDRESS:	
		STREET 1:		13403 NORTHWEST FREEWAY
		CITY:			HOUSTON
		STATE:			TX
		ZIP:			77040

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			DICKERSON J ROBERT
		CENTRAL INDEX KEY:			0001207709

	FILING VALUES:
		FORM TYPE:		4/A
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-13790
		FILM NUMBER:		081122516

	BUSINESS ADDRESS:	
		STREET 1:		6110 PEBBLE BEACH
		CITY:			HOUSTON
		STATE:			TX
		ZIP:			77069
		BUSINESS PHONE:		2813979568
</SEC-HEADER>
<DOCUMENT>
<TYPE>4/A
<SEQUENCE>1
<FILENAME>rrd220979.xml
<DESCRIPTION>FORM 4/A
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0303</schemaVersion>

    <documentType>4/A</documentType>

    <periodOfReport>2008-10-08</periodOfReport>

    <dateOfOriginalSubmission>2008-10-10</dateOfOriginalSubmission>

    <notSubjectToSection16>0</notSubjectToSection16>

    <issuer>
        <issuerCik>0000888919</issuerCik>
        <issuerName>HCC INSURANCE HOLDINGS INC/DE/</issuerName>
        <issuerTradingSymbol>HCC</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001207709</rptOwnerCik>
            <rptOwnerName>DICKERSON J ROBERT</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>C/O HCC INSURANCE HOLDINGS, INC.</rptOwnerStreet1>
            <rptOwnerStreet2>13403 NORTHWEST FREEWAY</rptOwnerStreet2>
            <rptOwnerCity>HOUSTON</rptOwnerCity>
            <rptOwnerState>TX</rptOwnerState>
            <rptOwnerZipCode>77040</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>1</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>0</isOther>
        </reportingOwnerRelationship>
    </reportingOwner>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2008-10-08</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>M</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>37500</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>16.80</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>101580</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2008-10-08</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>S</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>18625</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>22.6545</value>
                    <footnoteId id="F1"/>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>82955</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2008-10-08</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>S</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>18875</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>21.7459</value>
                    <footnoteId id="F2"/>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>64080</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <derivativeTable>
        <derivativeTransaction>
            <securityTitle>
                <value>Option to Purchase</value>
                <footnoteId id="F3"/>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>16.80</value>
            </conversionOrExercisePrice>
            <transactionDate>
                <value>2008-10-08</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>M</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>37500</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>16.80</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <exerciseDate>
                <value>2004-01-03</value>
            </exerciseDate>
            <expirationDate>
                <value>2009-01-03</value>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Stock</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>37500</value>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>0</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </derivativeTransaction>
        <derivativeHolding>
            <securityTitle>
                <value>Option to Purchase</value>
                <footnoteId id="F3"/>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>21.37</value>
            </conversionOrExercisePrice>
            <exerciseDate>
                <value>2005-12-20</value>
            </exerciseDate>
            <expirationDate>
                <value>2009-12-20</value>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Stock</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>18750</value>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>18750</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </derivativeHolding>
        <derivativeHolding>
            <securityTitle>
                <value>Option to Purchase</value>
                <footnoteId id="F4"/>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>30.85</value>
            </conversionOrExercisePrice>
            <exerciseDate>
                <value>2007-01-05</value>
            </exerciseDate>
            <expirationDate>
                <value>2011-01-05</value>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Stock</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>12500</value>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>12500</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </derivativeHolding>
    </derivativeTable>

    <footnotes>
        <footnote id="F1">The price of $22.6545 represents a weighted average of sales prices ranging from $22.01 - $23.01.  Full information regarding the number of shares purchased or sold at each seperate price will be provided to the SEC, the issuer or a security holder of the issuer upon request.</footnote>
        <footnote id="F2">The price of $21.7459 represents a weighted average of sales prices ranging from $21.46 - $22.00.  Full information regarding the number of shares purchased or sold at each seperate price will be provided to the SEC, the issuer or a security holder of the issuer upon request.</footnote>
        <footnote id="F3">Option to purchase granted pursuant to the 2001 Flexible Incentive Plan.</footnote>
        <footnote id="F4">Option to purchase granted pursuant to the 2004 Flexible Incentive Plan.</footnote>
    </footnotes>

    <ownerSignature>
        <signatureName>Randy Rinicella as Attorney in Fact for J. Robert Dickerson</signatureName>
        <signatureDate>2008-10-14</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
-----END PRIVACY-ENHANCED MESSAGE-----