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In this example wouldn't they be winning $2000 and losing *$900 for a taxable gain of $1,100?

 

Additionally, I have a question with regard to the notion of "session" as it relates to sports betting: if I place a $2,500 wager and lose it on Monday, and then I place a $1,000 wager on Friday and win $5,000, should I report the $5,000 gross from my Friday "session," or should I report the $2,500 net income? Follow up: what if these wagers were placed on different sportsbooks? Thank you in advance!