Do I need to file returns in those two states because I won there? Tax Guide for Aliens.trains and gambling ROULETTE PAYOFF The following rules apply to casual gamblers who aren't in the trade or business of gambling. Gambling winnings are fully taxable and you must. $1, or more in gambling winnings from bingo or slot machines; Any other gambling winnings subject to federal income tax withholding. For more information on gambling income and losses, see IRS Publication , Miscellaneous. IRS Summertime Tax Tip , August 31, Español. 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. If you are a casual.