I would never dream of winning a game-jam anyway, so I'm not really worried about anybody winning 100 times in a row. For me its about ppl playing my game and giving me feedback/leave a comment if/how they enjoyed the game I created. If I get ppl to try my game and tell me about their experience, thats a win for me.
Thats the way I personally approach game-jams, also when I go though the submissions. I'm usually not focusing on the slickest games (especially in a beginners jam) but on random games. If I feel ppl put some effort in what was produced, I make sure I leave a comment because, again, thats what I get the most out of with game-jams.