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Be clear and state the answer right up front. About our credentialed tax rfport Skip To Main Content. The W-2G looks similar to the W2 you receive yearly from your employer. Reporting gambling losses To report your gambling losses, you must be eligible to itemize your income tax deductions on Schedule A. Gambling losses are reported on Line 28 of Schedule A.Learn more about the gambling winnings tax and form w-2g from the tax experts at H&R Block. Here's how to enter your gambling winnings and losses in TurboTax if you did TurboTax will put the winnings and losses in the right places on your tax return. If you play the ponies, play cards or pull the slots, your gambling winnings are taxable. You must report them on your tax return. If you gamble.