Caesar's Palace -- slot machines Beginning cash = $315 Start time: 1:30 p.m. End time: 3 p.m. Ending cash = $290 Net win/(loss) = ($25)Net daily activity -- slot machines Wins = $115 Losses = $25 The next day you return to Bally's and play both the slots and Blackjack: 7/17/2013 -- Atlantic City, N.J. Bally's Wild West -- slot machines Beginning cash = $290 Start time: 1 p.m. End time: 2 p.m. Ending cash = $240 Net win/(loss) = ($50)Bally's Wild West -- blackjack Beginning cash = $100 Start time: 2 p.m. End time: 3 p.m. Ending cash = $0 Net win/(loss) = ($100) Table #234567Net daily activity -- slot machines Wins = $0 Losses = $50Net daily activity -- blackjack Wins = $0 Losses = $100 You did not win enough in one pull to get any additional Form W-2Gs at Caesar's or the next day at Bally's. The $175 in net losses from the two days from slots and blackjack could be included in gambling losses claimed on Schedule A if you itemize. By reporting $115 as gambling winnings on Page 1 of your Form 1040 instead of $1,300, you reduce your AGI by $1,185. While your net taxable income, $0, would be the same whether you reported $115 or $1,300 on Page 1 and were able to deduct losses on Schedule A, your actual tax liability may be less by claiming the lower amount of winnings. And if you are not able to itemize and claim losses you will certainly pay less federal income tax by reporting only $115 as your winnings. Not being a gambler, I do not know how detailed the information you get from using your Player's Club cards is. It is possible that printouts would support the individual activity by date you have entered in your book. Do not, however, assume the printout of card activity is enough proof -- you should still maintain your own contemporaneous gambling log.