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Thank you Recently, my boyfriend and I won a wlnnings contest, with a prize of 15k. Provided we have an acceptable gambling diary detailing wins and losses for the year. Most states also tax gambling income, either as a flat percentage rate or on a graduated scale commensurate with the amount of gambling winnings taxation winnings. More Products from Intuit. Wagering gains or losses in 1 year cannot be used offset losses or gains in another year nor can wagering losses be used to offset non-wagering income. Racing also offers a variety of ways to bet.Taxes on Gambling Winnings and Deducting Gambling Losses. In gambling, there are winners and losers But even the winners can be losers if they don't pay their taxes! Taxes on gambling winnings. Have you placed your Super Bowl bets in the office pool? Don't feel guilty. Gambling is inevitable. Thankfully, you can deduct gambling losses as well, which often helps to even out the taxation. How to Report Gambling Winnings. You will receive a Form W-2G from an institution that has issued your.