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Yes, you do. Gambling winnings are taxable income and must be entered on your tax return.
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
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
2018 Standard Deductions:
Single $12,000 (+ $1600 65 or older)
Married Filing Separately $12,000 (+ $1300 65 or older)
Married Filing Jointly $24,000 (+ $1300 each spouse 65 or older)
Head of Household $18,000 (+ $1600 65 or older)
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