I've won a few.
I've won a few video games and accessories from a multitude of magazine contests and such, I was the national champion of Magic: The Gathering for a year in the 90's, but the crown jewel was winning a writing competition for The Last Samurai. I got a trip to London (where I'd been, ironically, only two months earlier), all-expenses paid, a stay at a luxury hotel, £1500 of pocket money, red carpet treatment at the premiere for the movie, a leather bag full of promotional material for the movie like clothing and behind the scenes books, got to meet Tom Cruise, and a fancy dinner and cocktail at a Japanese restaurant. All that was accompanied by a film crew from a TV channel who did a story on us (I got to take my sister with me).