![]() ![]() ![]() If you win above $5000, the casino or sportsbook must withhold 24% and is obligated to issue you Form W-2G, which will document their withholdings. If you win under $5000, there is no withholding, but it's still potentially subject to taxes. You will be required to pay taxes on gambling winnings with sports betting apps, sites and retail sportsbooks in Massachusetts. Reporting gambling winnings is the responsibility of every Massachusetts resident, however small the wins. Are My Gambling Winnings Taxed in Massachuestts? Gambling problem in Massachusetts? Call 1-80 to speak with a trained specialist free and confidentially 24/7. Massachusetts bettors must be 21+ and present to place wagers in the state.
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