When I was 22 I went to Vegas for the first time and learned how to play blackjack on one hour flight down. I ended up winning about $5,000. Paid for the trip (obviously) and then paid off my car. That was the only time I ever played. Then, on my 25th birthday I went to Las Vegas again and won $900 on a slot machine. It was a Saturday night and the money lady (don't know what they are called!) took forever to come and cash me out. When she did, she left my credits in the machine (or I did, I don't know -- I had no idea what I was doing!). Well, we had reservations for dinner and so I decided to hurry through the credits. I kept winning a little here and there and then doubled my bet and what do you know... I won $1,800 about ten minutes later.
When I was about 28 I won a raffle at a charity event for an all expense paid trip for two to Ireland. I'd only bought one $10 ticket.
Let's see... Recently I won a membership to a professional group and saved the company $400. Then, at the same event, I won a $100 gift certificate at a nice restaurant, which I gave to my sister as a wedding present. Turns out the restaurant where the gift certificate was to was where they had their first date. I got serious brownie points for that.
I suppose I've been pretty lucky!