I won $1000 playing bingo. It was pretty exciting.
I won a 20" TV in a drawing at a car show. And I got 5 out of 6 numbers in the lotto too. But it only paid $474.
Last year at my department’s Christmas party I bought 3 tickets for the raffle and won on 2 of them. I got a new printer (which was good since my old one was working on dying) and a nice big gift basket of soap/bath salts/etc.
I won a bottle of (bad) champagne on our honeymoon for being the best male hula dancer in a contest at the resort where we were staying.
And $7 on a lottery ticket a couple of months ago.
And our President reminds me that I won several hundred dollars in a tax rebate this year, merely for having children listed on my tax return.
That’s pretty much it. Do any of those count? 
Won a drawing at a regional meeting of our newspaper group for a pair of season tickets to a nearby ski resort - sold them for $1,100, which nearly caught me up on my bills.
Other than that, just odds and ends. A whole box of Mr. Goodbars from a radio station trivia contest in the early 70s. Had a lot of fun with that.
I won a TV in a 50-50 raffle at the local town fair when I was 12. It wasn’t a big TV, mind, but when you’re 12 years old it’s darn cool to have your very own teevee.
The previous year, in the very same raffle, I had won $125. I think the next year the raffle organizers didn’t want me to get a ticket.
The biggest prize I ever won in a game of chance was $400 when I got 5 out 6 numbers in the Massachusetts lottery (Megabucks, I think). I also hit the daily number on two out of three times I played it for a total of about $75 (I was doing 1- and 2-number picks). I quit playing after getting a job where I sold tickets (and saw just how many tickets get sold and how few come back as winners), so I’m one of the few to ever come out ahead on the lottery.
The biggest prize I ever won in an actual contest was a $300 second prize (plus a VCR for my school) in a high school quiz bowl.
I also won free movie tickets from a radio station, but seeing as how they were for Ghostbusters 2, I don’t think that should count.
My Granny won a sheep (no - really) at a farm show
She gave it back
He kept it for a little over a year, couldn’t afford the $25K~ in taxes to keep it. Enjoyed it while he had it though.
I’ve won loads of prizes from puzzle and trivia contests, over the years. The biggest ones?
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A trip to Hawaii, from the Family Channel’s old interactive game shows
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A trip to St. Martin, also from tje Family Channel’s interactive game shows
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A trip to Ireland, from a local pub’s weekly trivia games
Beyond that, I’ve won a food dehydrator, dozens of concert tickets, videos, CD’s, DVD’s, a coffee table, some sneakers, and a TV.
Also a few million t-shirts and coozies.
I won $50 on an Instant Lotto ticket this summer when I was living in Rochester, NY. One of those “Cash Word” ones where it’s like a crossword puzzle and you make as many words as you can from your letters. I couldn’t believe I made 7 words and I re-checked it about 12 times. Made me very happy and bought my groceries for the month.
In high school I won a case of Pop-Tarts from the Kellogg’s website. They had this slot-machine game that was like a toaster and the slot-handle was the toaster knob. If you got three Pop-Tarts logos in a row you won a case of Pop-Tarts. So I sat there for 45 minutes pulling the little toaster knob until I won. Do you have any idea how many Pop-Tarts are in a whole freaking case? A lot. And when they’re all one flavor… I don’t like Pop-Tarts anymore.
My dad won an eight-day, all-expenses-paid trip for four to Walt Disney World. That was fun.
I won a trip to Mexico about 15 years ago in a school contest.
I won $750 at Bingo once.
I know someone who won a limo in a lottery. They kept it.
When the Lottery first started in my state, within the first year, two people my Dad knew won big at different times.
I’ve won various small prizes from radio stations and newspapers.
I, personally, have won only tiny stuff: 2 tickets to The Rocky Horror Picture Show; $36.00 in a 50/50 raffle; a cooler full of picnic stuff; a few other odds and ends.
Last year, my nephew hit the lottery for $2,000.00 just before Christmas. His Mom and sister got great presents!
My BIL won a new car at a wheel of fortune at the carnival some years ago.
In 5th grade (1991) I won first place for my division in the Walt Whitman Birthplace Association’s (something like that) annual poetry contest. I got to go to Whitman’s house in Huntington, won a $50 savings bond and a book store gift certificate, and got to meet Allen Ginsberg.
I won a 4 day cruise to Mexico. Ended up costing me about a grand for various fees and to take the youngin. Still a deal, and it wasn’t too bad.
She told me she loved me like a brother. She was from Arkansas, hence the Joy!
I won a yo-yo. I almost won a million dollars from McDonalds - I had 1/2 of the winning game piece at home, and found the other half while vacationing in Arizona. I lost it on the flight home. Seriously.
Biggest thing I’ve won is 2 tickets anywhere American Airlines flies (won at a bridal show). We used them for our honeymoon trip to Jamaica. 
I’ve won a few things from a local rock station. Last spring I won the Six Feet Under first season DVD, as well as lift tickets to a snowboarding/ski resort (I just passed those on to hubby). At events for the radio station, I’ve won 2 t-shirts and a CD.
Just last Friday I called in and will be getting the X-Men 2 DVD in the mail (plus all sorts of related merchandise–Xmen shirt, game, etc.).
Raffles are my thing, too. At a tack store nearby, I won about $200 worth of equestrian equipment back in August.
I like to win stuff. 
Dunno if it counts as a contest, but a few years back there was a pet store that was celebrating its grand opening not too far from my house. They were holding a ‘herby-derby’ hamster race with the hamsters running in plastic wheel-powered race cars. My hamster Smokey won first place, which was about 200 bucks and tons of free pet supplies (a lot of money for me at that time). I figured that hamster more than earned her keep (and yes, I have video of that race).
Other than that, nothing. My brother won a free Gamecube and games not a month after selling his old one on eBay, and a friend of mine won one of the first Playstation 2s that came out, but I’m lucky to win a free Coke these days.