Where did you see on IRS.GOV that someone should issue a 1099-MISC for each win over $600? That's not the way the IRS wants you to operate.
On the IRS page about the 1099-MISC, it says:
"File Form 1099-MISC for each person to whom you have paid during the year (emphasis mine):
- At least $10 in royalties or broker payments in lieu of dividends or tax-exempt interest.
- At least $600 in:
- Rents.
- Prizes and awards.
- Other income payments..."
That is, if the sports website has paid in the aggregate $600 or more to a bettor over the course of the year, the sports website will send the bettor and the IRS (each) a 1099-MISC. If a bettor wins three bets of $201 each, he/she would receive one 1099-MISC for $603. If the bettor wins three bets for $601, the bettor will get one 1099-MISC for $1,803, not three 1099-MISCs for $601.
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