I enter contests a lot, and I win a fair amount. The best thing I won was a year's supply of Haagen Daaz ice cream . And a Weider home gym - that was a really awesome thing to win (helped exercise off the ice cream pounds lol).
I've won a trivia question in a DIY meeting, and I won some lingerie in an offsite contest, but the big one's here on Ef...? No =( =( =( Which makes me really sad cause there's been at least two that I can remember that I really really wanted.
I've won many giveaways - some pretty cool stuff too! But honestly, you have to enter and enter and enter to win. I was on a roll for awhile but haven't entered in any for a few months now. If you want to win, you have to dedicate some serious time to entering them.