Gambling losses can be deducted up to the amount of winnings if you itemize deductions. You must report all gambling winnings on your tax return — regardless of whether you receive a W-2G. For winnings of $600 or more , and at least 300x your wager,, the casino issues a W-2G form and reports the amount to the IRS. U.S. casinos are required to report gambling winnings to the IRS. (more…)