I've never won anything. However my mom was a contest addict. She would get this newsletter and her hobby was just entering contests. Off the top of my head she won several bicycles, a real nugget of gold, several video games, a power glove, gift certificates to restaurants, and an all exense paid ski trip to Aspen in the "Find the Energizer Bunny Sweepstakes."
$3 from matching three numbers, from when I bought a few back when Texas lotto first started. Also might've won a few bucks from scratch off tickets. No gambler's luck what so ever. Even the couple of times I went to casinos with friends, I pretty much never win anything worth a damn. Not even token winnings that are suppose to draw you in.
I won 500 bucks recently on a "Run the Table" scratchoff. Before that the most I ever won was 75 bucks on a scratchoff. I used to have pretty good luck winning concert tickets. I saw Nine inch Nails, a Buzzfest, Big Head Todd and the Monsters with the Dave Matthews Band (Yes, that's how it was billed at the time), Smashing Pumpkins etc.
Rockets Bobblehead. I win contests at work fairly often, it is usually drawings from perfect attendance and things like that. Prizes are usually small like gift cards.