It depends and it's ambiguous as many tax rules can be. Each session would be each wager during the specific time frame and of the same type.
Keep in mind that the IRS will not follow each separate court case, but it's possible to site a court case if you are questioned to see if the IRS believes and agrees that it meets your similar criteria.
- 'This Court has also recognized the practical difficulties of tracking the basis of each wager individually in a session of like play.' (From the court case referenced.)
To reiterate the IRS tax rule for gambling winnings:
Gambling Winnings
A payer is required to issue you a Form W-2G if you receive certain gambling winnings or have any gambling winnings subject to federal income tax withholding. You must report all gambling winnings as "Other Income" on your tax return including winnings that aren't reported on a form. .
Gambling Losses
You may deduct gambling losses only if you itemize your deductions and kept a record of your winnings and losses. The amount of losses you deduct can't be more than the amount of gambling income you reported on your return. Claim your gambling losses up to the amount of winnings, as "Other Itemized Deductions."
@russell_gerhard1
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