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All income is taxable and gambling winnings are considered income. When you win, the entity paying you will issue you a Form W2-G, Certain Gambling Winnings, if the win is large enough. Fantasy League Winnings Are Taxable If you win your Fantasy football league, it's all taxable income in the eyes of the IRS. It may also be possible to establish your losses by keeping some type of detailed log. They could treat 80% of the contribution as a charitable deduction.

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