My Mom would win stuff all the time, once she won a new car at a church auction, won lottery tickets like every other time she played them. I have no idea if this had anything thing to do with it but she could spot a 4 leaf clover in any group of them that she'd see.
Me, well as the song goes, if it wasn't for bad luck I wouldn't have any luck at all (at least at winning contests, can't complain about the life stuff that much).