I won a Super Mario Brothers game cartrdige for NES from a scratchcard in a potato chip bag (Hostess) contest.
I won a $500 scholarship from the Officer Wives Club when I was 18. I used the money to buy clothes, and went to live in a commune for a year. Never went to college.
I feel kinda bad about that now:(
A few years back, the ReBoot website had a contest for the best suggestion for a web game. The grand prize was a publicity still autographed by one of the voice actors. I didn’t win, but I got an honorable mention, and for that I recieved a pewter keychain with the show’s logo on it. I occasionally wear it on a heavy chain around my neck, like dog tags. I consider it my official Badge of Geekdom™.
Also, I won a plush hippopotamus in a raffle at a Christmas party once. I named him Hamlet, for no particular reason.
I won $50 for being the best dancer one night at a nightclub.
Funny thing is I didn’t much feel like dancing that night, was really just there to have some drinks. But when they announced the contest and put on “Groove is in the Heart”, I put myself at the edge of the upper level of the dance floor, so I was visible to the judges, and proceeded to throw down, cut the rug, as it were. Halfway through the song, I was given the envelope as the winner. Then I went and sat down and didn’t dance anymore that night. $50 for a minute and a half of work? I wish I could get paid like paid all the time.
In college I won a contest for coming up with a mnemonic for the Stellar Spectral Classification order. The prize was a stack of the punch cards that computers used to use in the olden days. I thought that was really cool. (It can’t have been that good a mnemonic though, because I can’t remember it. The classic one is “Oh be a fine girl. Kiss me right now. Smack!”)
I won a portable basketball system a few weeks ago. I won it the week before we moved into our new single-family home, and considered it a good omen. 
My hubby and I shoot baskets almost every evening after dinner. It was a great prize.
I’ve won a few interesting things-
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3D sound card (yes, 3D sound card) from Diamond Multimedia, after purchasing a Voodoo II and sending in the registration card; I was the guy who won the “register now and you could win” grand prize, which promptly took up closet space.
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$100 door prize at a honky-tonk a friend of mine’s band was playing at.
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Scads of concert tickets and albums off college radio
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a Budweiser barbeque grill package from a radio contest
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And, fifteen minutes ago… tickets to go see Grammy Award Winners Nickel Creek Tonight at the Georgia Theater in Athens, GA.
Well, in my BIG chance to win a pile, on “Who Wants to Be a Millionaire,” I choked. I never even made the hot deat, and never answered any questions.
Still… I’ve won some very cool stuff in my day. The two best came from Pat Robertson. Seriously! About ten years back, the Family Channel had interactive game shows that you played by phone. In their Trivial Pursuit game, I won a trip to St. Martin, and later to Hawaii.
And just last year, I won a trivia contest at a local pub for which the prize was a trip to Ireland (my wife and I did that last fall).
Beyond that, I’ve won dozens of CDs, concert tickets, books, t-shirts, free dinners, small cash prizes, etc., from a variety of puzzle and trivia contests (mostly on the radio).
I don’t win anything. I am still a sucker.
You should all thank me.
When I was a senior in high school I won a trip to England from MTV. Twisted Sister was launching a tour in England and MTV sent 102 people (one winner from each state, plus guest, along with an extra pair from Vermont because they drew a Vermont person for Utah by mistake) to be “Twisted Commandos” invading England. We toured London and went to the opening night concert at Hammersmith Odeon, all 102 of us dressed as lead singer Dee Snider.
I don’t win things. I couldn’t win a raffle if you put my name in a box with a hundred other slips, all with my name, and nothing else.
But once I won something. The absolute, only time ever. Back when Tina was still doing the monthly quiz over at realworld.com, she’d take all the folks who got all right answers and draw one at random. So I answered ten questions about Peter Gabriel, and I won the quiz! I got a Realworld messenger bag and a Peter Gabriel Hard Rock Cafe T-shirt, and a Realworld T-shirt. The T-shirts have bitten the dust, but I still use the bag.
I won a 19" TV in a drawing. And I got 5 out of 6 numbers in the Colorado Lottery. Got $474. Used it to buy a Fender Stratocaster guitar.
A few weeks ago I won a free DVD and audio CD from Comedy Central. I entered “Minot ND” in the Insomniac ‘We need new towns to go to’ contest, and I was one of 100 first prize winners.
The DVD had five episodes, and the CD is about an hour or so of Attel’s standup (which ain’t bad).
Tripler
If he did come here, I have no idea where he’d go. 
I’m pretty lucky and I’ve won lots of fun stuff, but nothing major.
My husband and I went to Vegas to visit my dad for a week, and we won $2000 the second day. That was great because we only had about $200 spending money when we got there. We took my dad and his other kids to the Medieval Dinner and Tournament at the Excalibur. The next morning we met up for breakfast and on the way out of the restaurant my dad put a quarter in a random machine and won $500.
I won a Harry Potter tee shirt at the Harry Potter website for answering HP trivia questions.
I won $300+ the very first time I played the NY Daily Numbers. I had just turned 18 and my grandma sent me to play her numbers. Man was she annoyed that night when I won after betting $1. I was also very lucky when I went to Bingo with her, much to the chagrin of all the old ladies there.
I won a portable CD player at work a few months ago, in a random drawing.
I also won $50 last week at work for some stupid promotion.
My mother won a year’s suppy of Special K cereal. The bad thing was that they sent it all at once – one case of 12 huge boxes. I ate a lot of cereal that year.
I went to Atlantic City for the day back in October 1998 during my 2 weeks holiday from work. I’d never been, before, so i just parked ina parking garage and walked up and down the boardwalk for a while, marveling at how hideously ugly all of the casino buildings were. Finally I went in to Trump’s casino, and got $20 worth of quarters and put them in one of those big plastic cups and went cruising looking for the hot slot machine, which is another way of saying I wondered around for 30 minutes trying to find a quiet spot. No such luck, so I finally said the hell with it, and dropped 3 quarters in one machine and pulled the arm.
Next thing I knew lights were flashing, bells were ringing and quarters were overflowing onto the floor. It took 19 of the big cups to hold them all, and when I converted it to bills, I ended up with a little under $9,000.
That was nice!
Of course, I immediately spent it all on lap dances.
As if!!!
When I was working at L.L. Bean during peak last year, every week they would have a $50 drawing, which I won 4 times, including 3 in a row, which made some of the regular employees a bit upset.
Also, during peak, there was a special drawing for those employees who came on on their off day to help get through the overflow of orders that needed to be processed. I won a gift certificate for $100 worth of groceris from Hannaford
An R2-D2 cooler from Toys R Us back when Episode I was coming out. It was a register-once-a-day-online kinda drawing and I just added registration to my usual morning office routine. It’s about 2.5 ft high and I have nothing to do with it, so it sits in the office under the white board.
I’m so jealous of the R2-D2 cooler!!
I’ve won odds & ends, but my stand-out was back when I was living on the res. The last game of bingo one night, I won a live rooster. In a cardboard box. A very old, angry rooster. My dad shot him. My mom made rooster salad. Yes, it tasted like chicken.