<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0609</schemaVersion>

    <documentType>5</documentType>

    <periodOfReport>2026-08-31</periodOfReport>

    <form3HoldingsReported>0</form3HoldingsReported>

    <form4TransactionsReported>0</form4TransactionsReported>

    <issuer>
        <issuerCik>0001099369</issuerCik>
        <issuerName>DESTINY MEDIA TECHNOLOGIES INC</issuerName>
        <issuerTradingSymbol>DSNY</issuerTradingSymbol>
        <issuerForeignTradingSymbol></issuerForeignTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001407487</rptOwnerCik>
            <rptOwnerName>Vandenberg Fred</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerNonUSAddressFlag>true</rptOwnerNonUSAddressFlag>
            <rptOwnerStreet1>400 - 22 E 5TH AVENUE</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>VANCOUVER</rptOwnerCity>
            <rptOwnerNonUSStateTerritory></rptOwnerNonUSStateTerritory>
            <rptOwnerCountry>A1</rptOwnerCountry>
            <rptOwnerZipCode>V5T 1G8</rptOwnerZipCode>
            <rptOwnerStateDescription>BRITISH COLUMBIA, CANADA</rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>1</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>0</isOther>
        </reportingOwnerRelationship>
    </reportingOwner>

    <aff10b5One>0</aff10b5One>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Shares</value>
            </securityTitle>
            <transactionDate>
                <value>2026-08-24</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>5</transactionFormType>
                <transactionCode>A</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
                <footnoteId id="F1"/>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>33571</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>0.57</value>
                    <footnoteId id="F2"/>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>485555</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <derivativeTable>
        <derivativeHolding>
            <securityTitle>
                <value>STOCK OPTION (RIGHT TO BUY)</value>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>0</value>
                <footnoteId id="F4"/>
            </conversionOrExercisePrice>
            <exerciseDate>
                <footnoteId id="F4"/>
            </exerciseDate>
            <expirationDate>
                <footnoteId id="F4"/>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Shares</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>0</value>
                    <footnoteId id="F4"/>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>100000</value>
                    <footnoteId id="F3"/>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </derivativeHolding>
    </derivativeTable>

    <footnotes>
        <footnote id="F1">Purchased under Employee Stock Purchase Plan, which transaction is exempt under Rule 16b-3(c) of the Securities Exchange Act of 1934. Represents the aggregate of 23 purchases made between October 7, 2025 and August 24, 2026.</footnote>
        <footnote id="F2">The price reported in Column 4 was converted from the Canadian weighted average price of C$0.79 to USD using an exchange rate of CAD $1.3840 = USD $1.00.</footnote>
        <footnote id="F3">This balance represents previously reported transactions.</footnote>
        <footnote id="F4">80,000 stock options (right to buy common stock) are expiring on November 1, 2026 with exercise price of $1.50, 20,000 stock options (right to buy common stock) are expiring on July 25, 2028 with exercise price of $0.85. All stock options were fully exercisable as at August 31, 2026.</footnote>
    </footnotes>

    <ownerSignature>
        <signatureName>/s/ Frederick Vandenberg</signatureName>
        <signatureDate>2026-10-09</signatureDate>
    </ownerSignature>
</ownershipDocument>
