Certain special rules apply to gambling income, and there are strict recordkeeping requirements. Nonresident Alien Income Tax Return.roulette online fun POKIES ARISTOCRAT You may deduct gambling losses only if you itemize your deductions on Form , Schedule A (PDF), and kept a record of your winnings and. You may deduct gambling losses if you itemize your deductions. You can deduct your losses only up to the amount of your total gambling winnings. You must. Gambling losses are indeed tax deductible, but only to the extent of your winnings. Find out more about reporting gambling losses on your tax return.