You are eligible to itemize deductions if your gambling losses plus all other itemized expenses are greater than the standard deduction for your filing status.top uk gambling SMALL WOODEN ROULETTE WHEEL You may be able to deduct gambling losses if you itemize deductions. You CANNOT deduct more than the amount of gambling income you. You may deduct gambling losses only if you itemize your deductions on Form , Schedule A (PDF), and kept a record of your winnings and. 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.