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According to the IRS, you're able to claim gambling deduction for the business use of a part of your home only if you use that area regularly and exclusively:. Though it is a business trip, those filers can't deduct the whole cost of the family trip as a business expense. As a result, y ou can end up owing taxes on winnings reported to tax IRS even though your losses exceed your winnings for the year. Enter your annual expenses to estimate your tax savings. Many believe that they can simply deduct deduction cost of their home computers by claiming a home office. One arrested as cops tightly control white nationalist rally. It would be nice if there were a 5th Amendment exception allowing you to avoid paying taxes.Report any gambling winnings as income on your tax return. Be sure you itemize to deduct gambling losses up to the amount of your winnings. You can also deduct your gambling losses but only up to the extent of your winnings. Any other gambling winnings subject to federal income tax withholding. You may be able to deduct gambling losses if you itemize deductions. Income Tax - Chapter 28, Miscellaneous Deductions - See Deductions Not Subject to.