First few bets that I've ever won were ESEA matches, then ESL One rolled in. I won big on Epsilon when they weren't favored to win. Then I was hoping NaVi would win their best of three... I knew they were going to lose when I saw that Nuke was going to be the third map.
Long story short, I've won big and lost big. And then NiP decided to actually play and won ESL One.