Actual results will vary based on your tax situation. In the case of a wagering transaction with respect to horse races, dog races, or jai alai, all wagers placed in a single parimutuel pool and represented on a single ticket are aggregated and treated as a single wager for purposes of determining the amount of the wager. See paragraph c 5 ii of innternal section for a special rule relating to the time for making deposits of withheld amounts and filing the return with respect to those amounts.online roulette game fun SEARCH GAMBLING BINGO BLITZ 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. 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. For purposes of this title, any standard deduction allowance under subparagraph (E) shall be .. (q) Extension of withholding to certain gambling winnings.