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You win both ways in a situation.
"Since i'm off Saturday, I can go to the party and the club too, so thats a win-win situation!!"
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A situation in which you benefit twice and no one else benefits at all.
You: if you buy me a hotdog and give me the change then it's a win-win situation!
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Sarcastic term for a "stacked deck" set of circumstances dat allows one lucky person to come out on top no matter which way things go.
Horny stud: How's this for deal --- if I win this game, YOU'LL agree to have sex with ME, and if YOU win, I'LL agree to have sex with YOU...??
Hot chick: Yeah, right --- THAT means l'd hafta spread my legs for you in ANY case --- talk about a "win-win situation"! :P :P