Gambling To enter the W-2G   or other documents For your Gambling winnings--Go to Federal>Wages & Income>Less Common Income>Gambling Winnings You can enter your winnings, and then keep clicking through the interview to enter gambling losses.   https://www.irs.gov/help/ita/how-do-i-claim-my-gambling-winnings-and-or-losses   Gambling winnings are taxable income.   Losses are an itemized deduction.   If you do not have enough itemized deductions to exceed your standard deduction, your losses will have no effect. https://blog.turbotax.intuit.com/income-and-investments/how-are-gambling-winnings-taxed-8891/   https://ttlc.intuit.com/questions/1900352-can-i-deduct-my-gambling-losses     2019 Standard Deduction Amounts   Single $12,200   (+ $1650 65 or older) Married Filing Separate   $12,200   (+ $1300 if 65 or older) Married Filing Jointly $24,400   (+ $1300 for each spouse 65 or older) ... View more