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Hello and thank you for using Just Answer.The only amount of your losses that you can claim on the Schedule A would be equal to your winnings. If you have $5000 in losses but $2000 in winnings the additional $3000 is lost a s a deduction but if the losses are equal to the winnings and still make you higher on the Schedule A than standard deduction use, yes you can itemize just by using the losses. I stress though, you cannot claim losses more than you show as winnings.Thank you in advance for clicking ACCEPT and Happy New Year.