I won $11.90 on a $2 bet on the very first horse race I ever bet on. Not much of a win, I’ll grant you; but then again, I was all of 12 years old at the time.
I need to head down to my local social club tonight… I had 12 correct picks in this weeks football pick 'em pool and that could be enough to win $50.
My best real gambling win was either winning $350 in a single $1/$2 no-limit hand at foxwoods(flopped a full house) or winning $850 online by beating out 1500 others in a $3 buy in no-limit tourney.
I always wanted to play poker in Vegas (low stakes - just for the atmosphere).
I entered several tournaments, then finally won a two table event. It was only $350, but it felt like a World Series! 
In 1974, my dad took me to Roosevelt Raceway (R.I.P.) on Long island and bet my picks for me. I figured out how to read the program, made my picks,and wound up picking 2 trifectas and a quinella on the card. We won $450.
I was eight.
Many years ago I was drug by my mother and grandmother to a bingo hall. I didn’t have much money at the time and bought a few cards to play. The big game that night was a 48 ball blackout game to win a new 1982 Chevy Cavalier. I bought 2 cards for the game. On ball number 42 I had all but B1 to win. Ball 48 was B1.
I had one problem though. To take delivery of the car, I needed to come up with about $1200 for taxes and license fees. I made a deal with the dealer to get $2000 under the table and he got an already paid for new car to sell meaning 100% profit for him. I put all but $200 into my bank account, 2 days later the state took the other $1800 for back child support.
I got a Royal Straight Flush (in Spades) playing Texas Hold 'Em on my Blackberry yesterday.
Needless to say I won the hand.
tonight… the Vikings hold on to cover the -3.5 point spread and I win my weekly pick-em league with a higher point total (47) than the next guy (45)…