Pay for TurboTax out of your federal refund:vodka roulette game WHERE IS GAMBLING ILLEGAL If you itemize instead of taking the standard deduction, you can deduct gambling losses up to the amount of your winnings. For example, if. The biggest single thing to know is that you can only deduct gambling losses for the year to the extent of your gambling winnings for the year. You can also deduct your gambling losses but only up to the extent of your winnings. Here are five important tips about gambling and taxes: Gambling income.