I won a XBOX 360 (along with the Kinect and 2 games) at a raffle in my mall last summer.

You?

A MacBook through my ISP back in '09.

I won Toy Story DVD box set from my local HMV before. Slaying

A 'you tried' prize at my school's athletics-themed year-end tournament in Elementary school.

Nothing

I got a participation ribbon at school for coming last in the sports carnival run

I won the Collector's Edition (US) of Batman Arkham Asylum from some online viral marketing campaign that Eidos and Rocksteady (Game Dev) were running, it was an amazing, well-constructed campaign.

Yes. In geography my teacher made a contest (kinda)
Everybody had to pick a country and make a powerpoint presentation about it.
I picked England and because I'm the best at making presentations in my class, i won.
The price was 2 weeks no geography homework

Yes. Awards, cash, scholarships, etc.

I won a free book on Goodreads last week.

Something at primary school and I can't even remember what it was

One time I won a digital camera out of one of those Stacker video game machines. I've also won a lot of concert tickets from radio stations.

yeah, I'm actually pretty lucky with that kinda stuff.

I've won at least 10 pairs of great shoes online, won a chocolate bar golden ticket thing my school was doing in middle school, a bunch of other stuff too

A lot of books and i have no intentions on reading them.

Yes. A pocket wi-fi. I won it by sending tweets in Twitter. And in school too, some awards.

Karaoke competition when I was 8.

Yes, I met Anthony Horowitz - the author of the Alex Rider series.

Rihanna tickets. Lady Gaga tickets. But a week before I was going to see Gaga I got a call from the radio station telling me she cancelled the show because of her hip problems