I won a box of Twinkies, $1000 on a scratch ticket, $500 on a slot machine, 1st speaker in 3 debates and 2nd speaker in another debate, honorable mention at the science fair, lots of JROTC awards, and a soccer ball.
A round trip for two to Australia.
Qantas was having a contest to see who could re-write a Christmas song to feature lyrics about Australia.
I re-wrote every Christmas song I knew, added in some re-written Beatles and Dylan, made up a crossword, and added a story describing how I envisioned the trip unfolding.
I don’t know if I won outright or just wore them down.
Australia was unsurpassably cool.
Nothing. Ever.
For Christmas one year, my Father bought me and my two sisters a hundred scratch-off lottery tickets. I was the only one who didn’t even win $2.00.
At a raffle, my then-BF bought three raffle tickets and I bought over 40 tickets. He won the tickets on Alaska Airlines.
I am the unluckiest person in the world when it comes to such things. No trophies, no awards, no nutt’n.
I won a UK regional Class 4 (50cc) karting championship when I was a wee lad. I was the youngest winner of a couple of school trivia and spelling contests.
I won a cheap AM/FM radio back in 1976. Piece of crap quit working after a few weeks. I won a radio contest for “name the governor’s plane” in Alaska a few years ago. The prize was a plastic model of the plane, which sits in a place of honor in a landfill somewhere.
- A trip to Chicago to train with a long-distance runner from Cooking Light magazine
- $5000 on my state’s scratch-off lottery TV show, thanks to my grandfather entering my name in the prize drawing from one of his tickets.
- Margarita mix and four margarita glasses from our campus GBLT group in law school
- Tickets to an Ani DiFranco concert for getting first place in NTN trivia at Damon’s while watching the Stanley Cup playoffs in college.
- I won tickets and backstage passes to Aerosmith during the Pump tour by correctly guessing that the #1 song on the local radio station’s Top 9 at 9 countdown would be the Bart Simpson Rap that their morning show put together. Unfortunately, we couldn’t find their street team at the show, so I didn’t get to go backstage. About 9 months later, the station called us up and asked us if we wanted tickets to Poison and Warrant, which I’d been trying to win all week to no avail. So I got to go to that show for free too.
I think that’s it.
Oh, nevermind, there’s #6. An Ohio State sweatshirt from one of those football pools with the grid of squares at Champps. That was the prize for the 3rd quarter…the prize for the 4th quarter was an iPod.
I won a hula-hoop context when I was 10. Got a weird looking stone pendant for it. Five years later I was flipping through my history textbook and discover that the pendant was a replica of some ancient Korean artifact depicting a smiling woman. Huh. I think I still have it somewhere.
Jeesh, after reading about everyone else’s luck, mine pales in comparison. I won two Candlebox tickets off of the radio once, which was pretty cool. I’ve shown horses for about six years now, and won a handful of classes. The best was when I took first place in pole bending, won 8$, and beat my mom by a few seconds!
Ooh… forgot my proudest win: a genuine Blue Peter competition badge.
Gave me free entry into all sorts of cool places, and for a 7 y/old in 1980s UK it conferred major social status in the playground 
I’ve only won one thing in my whole life. When I was about 10 years old, I won six tickets to see The Return of the Jedi from a drawing at a supermarket. I didn’t get to use the tickets though, because I had seen the movie already and my parents certainly weren’t going to take me to see it again.
Other than that, I never win anything. I have very bad luck when it comes to that sort of thing. Some memorable near-misses:
I won a drawing for a water ski from a boating store, but when I got there to pick it up, someone else had claimed they won it and took it for themselves. Since it wasn’t a brand they normally stocked, I was out of luck.
I hurt my ankle just before a small 5K road race and didn’t start, but had I run the pace I ran in another race two weeks before I would’ve easily won overall. The winner’s time was like 21:40-something, when I was running sub-20’s.
A former employer had a monthly all-hands lunch party thing with a few door prizes. The rules were that if you won before, you couldn’t enter again, with the idea that eventually everybody will get something. In the 3 1/2 years I was there I never did, because whenever they got down to a few people left they reset the whole thing.
I’ve never played the lottery or spent more than a few bucks in a casino, but I have won several drawings of the leave-your-business-card variety:
A small color TV
A $500 gift certificate to Best Buy
An Ipod (which I gave to a relative since I had already bought an IPod with the $500 Best Buy gift certificate).
A $250 gift card – forget if it was to a store or an Amex card.
I won two bottles of booze at a raffle once but that hardly counts since there almost more gifts than ticket holders
I won a bingo prize a long time ago–where you pick whatever’s on the gift table–but I forget what I picked.