1. Usually a casino/ online betting site reports the cash they gave you. So the payout, NOT the profit.
2. Depends.
If you walk in to a casino, wonder around playing slots and win 1,000 ten dollars at a time, nothing will be reported.
If you get a casino account and stick the card into the slot machine before you play and win 1,000 ten dollars at a time, the casino will report it.
If you win 1,000 playing cards, the casino will be aware when you cash in your chips and report the winnings.
For online sport betting, it would be the same as the person that puts a card in the slot machine. If the bets are all made from the same account, they will summarize for the year.
This is what they should do, not necessary what they do do.
When you have reportable winnings, you can offset with the cost and your losses for the year (up to the amount of winnings) you can't show a loss (unless you are a professional gambler and file Schedule C)
ONE MORE THING, if you do report gambling costs to offset the winnings, you can only do that if you Itemize Deductions. If use the Standard Deduction, the winnings will be reported, but none of the cost/losses.
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