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Get every deduction you deserve. Are they allowed to get their winning money? Refer to PublicationMiscellaneous Deductionswinings more information. When you win, your winnings are taxable income, subject to its own tax rules. Then you should probably gambling winings with them on filing your own tax return. Or do you have to claim your gross winnings. You must show the amount from Form Gambling or Form as other income on Line 21 of your income tax return.Gambling winnings are fully taxable and must be reported on your tax return. Gambling income includes, but is not limited to, winnings from lotteries, raffles. If you receive a certain amount of gambling winnings or if you have any winnings that are subject to federal tax withholding, the payer is. The IRS has strict rules surrounding the taxability of gambling winnings. And if you don't play by the rules, the government always wins.