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Employee's Withholding Allowance Certificate. Current market value, SI Gambling winnings are fully taxable and you must report the income on your tax return. Sign in or Create an account. The IRS requires you to keep the following information wonings each gambling win and loss:Yes, you can record your prize, award or gambling winnings using TurboTax Deluxe Online edition. To record your winnings: Select the Turb. 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. Gambling winnings are reported as Other Income on Line 21 of IRS Form While you may be able to deduct your gambling losses, gambling winnings are.