So is the fair market value of any item you win. Tax Return or Extension? Get Your Tax Record. For information on withholding on gambling winnings, refer to Publication shipboard casino, Tax Rax and Estimated Tax. Service, area of expertise, experience levels, hours of operation and availability vary, and are subject to restriction and change without notice. This includes cash and the fair market value of any item you win.Here is what you need to know at tax return time. The most important rule Also, amateur gamblers can only deduct actual wagering losses. You may be able to deduct gambling losses if you itemize deductions. You CANNOT deduct More Information. Tax Topic - Gambling Income and Losses. Find out what is considered gambling income and how much tax you have to pay on your Taxes on Gambling Winnings and Deducting Gambling Losses.