Actually I won a few times from TV Squad since it's beginnings.
One early contest(c. 2006) netted me $100 (although I wanted the iPod they sent a check) for highest rated comments. Now most of their contest hold no prizes but they do have lots of giveaways.
Several times for this Subtle Subtitles and I think a few others. I didn't track them all but I will from now on because it fills a void in my life.
I have won multiple times in a row so go on TV Squad and dare to challenge this week's contestants.