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Do you have to pay taxes on sweepstakes winnings? Yes, in the United States, any winnings from sweepstakes, contests, or lotteries are considered taxable income by the IRS. This means that if you win a cash prize or valuable items, you must report these winnings on your tax return. Do you have to pay taxes on sweepstakes winnings? The answer is a definitive yes, and it's essential to keep accurate records of your winnings to ensure compliance with tax regulations.