Article Highlights Gambling winnings must be reported as taxable income. Gambling losses may be deducted as an itemized deduction. Losses cannot exceed winnings. Losses must be documented. Winnings must include all winnings not just those shown on a W-2G. Good news...You can! However, the bad news is that gambling losses are only deductible up to the amount of your … [Read more...] about So You Want To Deduct Your Gambling Losses?