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You may cancel your subscription at any time from within the QuickBooks Self-Employed billing section. Credit or Debit Card. The bottom line is that losing money at a casino or the race j does not by itself reduce your tax bill. You cannot reduce your gambling winnings by your gambling losses and report the difference. Recommended Answer people found this helpful You can't put in gambling losses unless you first put in gambling winnings. Popular For Tax Pros. This includes items such as receipts, tickets or other documentation.If you itemize instead of taking the standard deduction, you can deduct gambling losses up to the amount of your winnings. For example, if. 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. You may deduct your gambling losses on Schedule A, Itemized Deductions. The deduction is limited to the amount of your winnings. You must report your.