I hardly win things. The last thing I remember winning was when I was probably around age 10 I entered my schools raffle and won that, but I wasn't there to recieve it and it was given to someone else. It doesn't really bother me when I don't win since I am so used to it and I never expect to win. So much so that I only enter competitions that I would enjoy doing whatever the entry requirement is (like having to create something).

Well IGN just did a competition over Easter using the 3DS Nintendo LetterBox (Swapnote in the US) app. You had to send in videogame-related images set around Easter. I entered just because I like drawing odd things on my 3DS and liked the idea of doing it for something. Now that it is nearly a week later I got a reply - I was one of the 6 winners!.

You can see all of them here (mine was the Kirby one). Now there were very few entries (it wasn't really promoted on the site) but I am still stoked I won. Although, now begins over half a decade wait to win something again...

Edit---

I won a 3DS e-shop voucher