My biggest bet has to be probably $1k... while playing $2-$4 No Limit Holdem at FullTiltPoker... that night I ran $25 into $100 playing $0.25-$0.50 Rush Poker... Opened 3 more tables and ran those $100 into $500 then moved to $0.50-$1 and so on. I ended up losing $1000 with a K high flush against A high flush... dude... I throwed up from the balcony... stayed awake partying. Next day at 2pm I won around $800 playing live.
My biggest bet won is winning 3 satellites in a row to win a $2500 international tourney package. The 1st satellite costed me $24.