I just heard back from the online sportsbook / casino and this is what they've stated...
Below is a breakdown of how sportsbook winnings are taxed.
Form W-2G:
- We will issue a W-2G form each time a player has a payout of $600 or more (no reduction for the wagered amount) and a return which is 300X the amount wagered.
- We will withhold federal income tax from the winnings if the winnings minus the wager exceed $5,000 and the winnings are at least 300 times the wager.
Form 1099-Misc:
- We will report prizes and awards that are not for services performed and are not a result of a wager whose aggregate amount is $600 or greater.
I then asked if the amount reported on the 1099-Misc is the total win / loss for the tax reporting year (assuming no individual payout meets the requirements for a W-2G)? So the $100 in the example above, not the $10,100. To which they replied that is correct.
