Sign in to QuickBooks Self-Employed via mobile app or at https:roulette jatek ONLINE GAMBLING GOOD You may deduct gambling losses only if you itemize your deductions on Form , Schedule A (PDF), and kept a record of your winnings and. IRS Summertime Tax Tip , August 29, You can also deduct your gambling losses but only up to the extent of your winnings. You can claim your gambling losses up to the amount of your winnings on Schedule A, Itemized. You may be able to deduct gambling losses if you itemize deductions. You CANNOT deduct more than the amount of gambling income you.