not to toot my own horn or jinx my luck *knock on wood* but im pretty decent at winning contests and such sometimes
about two years ago now, give or take a couple months, i saw Xfire was having a contest for a autographed copies of Pure Pwnage Season 1 on dvd. you had to enter to get into a fan chat with the cast, so that was a random draw. then in the chat, the cast chose 15 people out of like 100 who asked them the best questions, to get the prizes. I won a copy ;p took a while to get here but it is indeed awesome.
about a year and a half ago, i won an ipod nano in a random raffle drawing, 4gb silver, which yea the 4th gen nano is out now but at the time the 3rd gen (which it was) was literally brand new so it is indeed awesome.
last monday i saw a contest over on Evil Avatar's forum, for a random drawing for copies of Defense Grid. so i entered, they drew the prize winners today, and I won ;p I got my steam activation code very quickly, worked fine, had it downloaded within 5-10 minutes and been rocking it all day long, great game (if you love tower defense games, this one is epic).
i've won quite a few random raffles and drawings over the years, the ipod probably being the most valuable thing.