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May 16, The racint of horses break from the gate for the start of the Preakness Stakes. Get a personalized list of the tax documents you'll need. Sign in to QuickBooks Self-Employed via mobile app or at https: For Canadians, your gambling losses can be used to offset against the withheld taxes on horse racing wins while in the United States. For many of us, gambling means buying the occasional lottery ticket on the way home from work, but the Internal Revenue Service says that casual gambling also includes raffles, casino games, poker, sports betting—and, yes, even fantasy football.Gambling winnings are fully taxable and you must report the income on your tax return. but isn't limited to winnings from lotteries, raffles, horse races, and casinos. or have any gambling winnings subject to federal income tax withholding. Horseracing Wins As Treasury/IRS Issue Updated Tax Rules only the $1 bet on the single winning combination as the amount wagered. money made from horseracing, dog races and jai alai pari-mutuel betting, subject to withholding under Section (q) of the Tax Code.