2001 Ravens Super Bowl Win and 2010 NO Saints Super Bowl Win. Had both in futures before the seasons at 50-1 and 25-1 respectively, but when the Superbowl Matchups came, I loved the teams even more, and kinda went hog wild and bet far more than I should have.
My most satisfying though, was when I was a kid in School. Bet anyone who wanted some, that The Chiefs would beat The Vikes in Superbowl IV. No Points necessary. Probably won about $200 or so, which was pretty sweet for a dumb kid taking a 14 point dog on the moneyline.