Well, this episode finally appeared in syndication in the States (it was rerun during the 92-93 season, and also has apparently shown up in Canada before this). Here are some thoughts I had.
1. This episode is, I think, a bit overrated. Don't get me wrong, it's a great episode (the very beginning, until they link pinkies on the bet, is superb stuff), but after that they episode tapers off a bit. Before, based on my memories of when I first saw it, I would have rated it as my favorite. It's still in my top 5 after this repeat viewing, but it's no longer undisputed #1 (The Outing and The Boyfriend, Part 1 being up there for me).
2. On the "who won?". Obviously The Contest leaves it unclear as to whether George or Jerry won. Many people have brought up that George claims to have won in "The Puffy Shirt" when he gets the hand model job, but I would have to rate George as a very unreliable witness, since we know he's living like 20 lies. However, I think that Larry David has confirmed that George won (confirmed it off-camera, that is, not in any episode). This is too bad, as I would like to leave the question as "one for the ages" (like why Audrey wouldn't eat the pie)
3. Noone has commented on why they waited until April 29th to air it--Jerry's 42nd birthday!