I recently won an insulated travel mug with lid.
I don’t drink hot beverages. 
Second place in a drawing contest when I was 8 years old. Won a binder and 10 postcards of my drawing.
a big bunch of flowers in a lottery in a movie theatre.
A statuette for playing (and reaching second round) in the Dutch version of Jeopardy, five years ago.
Living in Las Vegas, sometimes good things happen.
About 7 years ago, my SO won $12,500 playing a quarter video poker machine - you had to get the Royal Flush, in exactly sequential order. Not an easy feat. Without even being aware of it, he hit it.
Nice surprise, well-needed - he had just been informed he needed major dental work and it cost over $10,000 to have it done. Perfect timing for the win.
About 5 years ago, I won $10,000 on a video Keno machine.
I used the money to go back to school (UNLV) and take some additional courses, which allowed me to start teaching at a local college. I also bought a laptop. All in all, money wisely invested from the winnings.
Granted, as is the case here in Las Vegas, it takes lots of losing to finally win something. Winning big doesn’t happen often enough as far as I am concerned - but I think we were both at least smart enough to take those windfalls and do something practical and good with the money.
Living here, I have met others who have had their share of “magic moments” with winning large prizes - one older guy (the mail delivery guy at the Law Firm where I used to work) won $85,000 on the big football pool at the local casino. Again - this is a guy who has been playing regularly for years - so it was not like he just walked in and won first time out. Other locals all have great stories - a woman I know got two Royal Flushes, back to back, on the same video slots - for a total of $4000. Many other stories, but people generally recall the good times, and don’t mention the 6 months where they didn’t win squat…Welcome To Vegas!
an easter egg in a maths competition, which had nothing to do with maths. It was to do a ‘study’ on pet food. Mine was the best.
I won a free handgun, a Beretta 96, simply by registering my name at the semiannual gun show hosted by my local gun range.
Only in America 
$100 bond and a casiotone keyboard, on a game show when I was 7
5G iPod Nano, at a fundraising raffle. That was especially sweet because my old Nano conked out 3 days before!
In monetary value order:
I won elected office in student council every year from 2 - 10th grades.
I won a commendation from the mayor of Pittsburgh for chairing a community revitalization project.
I won 52 $5 gift certificates (“free lunch once a week for a year”) from a local Wendy’s for dropping my business card in a fishbowl.
I won a fairly nice (for 2001) 28" color TV by dropping a business card in a fishbowl.
I won a $500 activities grant and a pizza party for the floor of my dorm at college by conceptualizing and creating the artwork for our holiday “open house” contest entry “Old Fashioned Country Christmas.”
I won a variety of prizes in about 40 different contests from a radio station, ranging from CDs to nominal amounts of cash ($15 - 50) to mani/pedis, front row concert tickets ($105/seat) and eventually a DVD player. Then they changed call letters and formats, fired all the DJs and stopped running contests. The weirdest of those prizes was a haircare set including a curling iron, straightening iron and blow dryer. The most useful of those prizes, beyond the DVD player, is George Foreman grill that I still use at least twice a week, though mostly as a poor woman’s panini press.
I won a half-scholarship to college based on being a National Merit semi-finalist.
I won one year’s lease of a Cadillac Escalade in a talent competition, for singing. I declined the lease and instead got the “real cash value” which was several thousand dollars.
Does it not work with cold ones?
My alma mater has this late night breakfast in the main dining hall just before finals week (to help relieve the stress of studying). They have a raffle, and the prizes range from the cheapo (plastic frisbees) to the fancy (iPods and laptops).
I won an electric guitar one year. I don’t play. I ended up giving it to my brother, who declared it a piece of crap. Actually, the last I heard he was fixing it up so that it’d be more playable.
The next year, as they were doing the raffle, they held up a package of KY Intense lube as the next gift. I turned to my friends and went “wouldn’t it be funny if I won that?”
Guess whose number they called?
It turned out to be kind of a crappy lube. I used it once and then stashed it away in a drawer.
Bowling tournaments, Taekwondo tournaments, the occasional lottery ticket.
But the most valuable thing I’ve ever won was SWMBO’s heart.
A couple of moderate slot prizes in Reno or Vegas, $750 and $1250, IIRC. Smaller ones as well.
A few hundred dollars a couple of times on California Lottery and Scratchers games.
A pair of Wrestling tickets in a radio contest - I didn’t go.
A few very small and insignificant consolation prizes in sweepstakes.
Joe
I’ve won several 1st place and ‘best of show’ prizes for my artwork, as well as a several-thousand dollar scholarship for my art. I won over $5,000 playing Bingo on my honeymoon. Other small things here and there.
When I was a kid, one of the local newspapers often had art contests for kids. I won (or came in 2nd) several of them. I won things like a stack of great books, circus tickets, sports tickets, and a cooler that I still use.
I won a 42" widescreen TV at a charity raffle. That was awesome.
I won a bunch of radio contests as a pre-teen/teen. The prizes were:
Pizza
Pizza
Pizza
Pizza
Pizza and Gallagher Tickets
I told my friends in college about my apparent talent for winning pizzas on radio station contests. One day, while we were listening to the radio, a pizza contest comes on. I calmly proclaim, “I’m going to win that pizza,” call in, and, sure enough, win the pizza, along with a pair of tickets to see Princess and the Pebble or something animated film with a similar name. I don’t remember, as I never picked up the pizza (it was two frozen pizzas) or the tickets for the movie, since it required me being somewhere at some ungodly hour for a college student like 8 a.m.
Come to think of it, I don’t think I ever cashed in on any of the pizzas I won, as they were always for some local place on the other side of town from me, and my parents were not about to trek fifteen miles for a pizza.
My pizza radio contest streak ended about four years ago, when I won some Harry Potter book-on-tape for answering a trivia question to which Jim Rice was the answer. (I believe it had something to do with what Red Sock Hall of Famer wore #14, or something to that effect.) I ended up donating whatever it was I won to a local school for the blind.
I won 200 pounds (Sterling) on the slots on the ferry from Dover to Calais on my 21st birthday. That was cool. I then won an additional 20 pounds minutes later explaining to my American tourist acquaintances how to play the slots.
I’ve won awards for my photography, a National Merit Corporate Scholarship, a bunch of academic bowl-type crap in 8th grade, and I’m sure a bunch of other stuff I can’t remember. But pizza, most often.
I’ve played one spin of roulette in my life. Put $40 on 17 and it came in.
Last year I won a prize pack in the fantasy league run in conjunction with the track & field world championships. This year I was third (out of 3000+ people) in USA Track & Field’s season-long fantasy league and won $100 and a prize pack…I was one dumb pick away from first place and its $2000 prize.
I’ve won more meaningless trinkets at road races than I can possibly count (although not a thing for any of the four I’ve won outright). Once my roomate beat me and got something useless while I won a gift certificate to the local pizza joint. I razzed him for weeks and didn’t even share the pizza.
Mostly petty things. Donkey Kong Jr. shirt and shoelaces in an arcade competition when I was 8 or 9, a giant pumpkin for correctly guessing its weight (which actually caused a small cheating investigation at my school, because I submitted an absurdly accurate answer as a joke, and it turned out to be correct), an album for setting a high score at an arcade that I wasn’t aware was running a competition, $50 on a scratch-off lottery ticket someone gave me as a gift, several albums for calling a radio station.
I’m absurdly bad at losing door prize draws; my work runs a door prize draw each Christmas, with ~100 prizes for ~300 employees, or around 1 in 3 odds. I’ve been there for 16 years and have never had my name pulled. A local convention that I attended twice annually for around 10 years awards door prizes with fairly good odds, and again I never win, while every time I take a friend, they win.
Since starting college part-time in 2002, I’ve amassed a ridiculous number of scholarships and awards, despite never being proactive enough to apply for anything (makes me wonder how much in scholarships I could have amassed if I’d actually applied for some). I’ve actually turned a profit on going to school since 2004 because of these things; it’s kind of nice to not have to worry about tuition or book costs.
My wife and I won the first time we ever set foot in a casino. We were driving near Atlantic City about 12 years ago, decided to see what casinos were all about, and stopped in Harrah’s. We had been playing the quarter slots next to each other for about 5 minutes when my slot machine started going ding-ding-ding and coins came tumbling out (this is when the winnings were in actual coins instead of vouchers). I turned to my wife to tell her, and her machine started going ding-ding-ding, coins tumbling, etc.
That detour paid for our trip, and for a while I thought casinos were the greatest thing in the world. I didn’t know why everyone didn’t play. I’ve become a bit more savvy since.
I won Carl Kasell’s voice for my home voice mail from NPR’s Wait Wait… Don’t Tell Me… I played the “Bluff the Listener” game and was able to correctly guess the true story.
When I was in college I guessed the number of coffee beans in a jar and won a Melita travel coffee maker, with mug and carrying case. It’s one of the best things I ever owned. I used it until it literally fell apart.