My best friend won a trip to disney land(the one in florida) by having the fastest lap time in a racing game at some convention. He took me because i trained him and taught him how to virtually drive. Actually he's a lot better than me, but i've beaten him once! All i had to do was get us to the airport. It was AWESOME!
Cooler at 38th Street Hooters during the Super Bowl in 2001. Ended up being a good deal....the ladies rode it around while i pulled it (obviously had wheels) and then at the end of the night...they all signed that top (and some phone numbers)
lets see , won a gigantic Hersey bar in high school some sell stuff to raise money thing, won a trip to New York from a former company I worked for,won a couple of 5,10,25 dollar gift cards from my current company also won two 100.00 gift cards from them and a 19in lcd tv and a couple of dollars here and there from the lotto.
i won $50 from a slot machine in Jamaica when i was 16... won a gift card from my work's Christmas party for $50 at Target... nothing else comes to mind