$500 on a scratch ticket I had to split with my girlfriend. She owed our teacher $5 on a Pats bet so I told her I'd pay him in 500 pennies as a joke. She ended up paying him $5 in cash, so then I just gave him the pennies, explaining the failed joke because what the hell was I going to do with them. He used to offer off scratch tickets in class every blue moon when having a contest or something. He gave her and I a $5 scratch ticket because he's a funny and nice guy, which we scratched at lunch and fround we won $500. Good day.
$50 on a road race in South Boston which I ran with a undiagnosed stress fracture. That race sucked.