Thank you for clarifying your position. Perhaps we're closer on this that it seems from reading the posts, just wording it differently.

Winning can also be not fun. Especially games like Chess. Playing a person that's no match for you guarantees a victory, but like you've said it's not as sweet. Losing every game in a tournament sucks, and it'd be hard to see the fun in it. There is still fun though. I doubt if the Chess tournament organizers would let you play the masters without going through some type of qualifying first. Of course if it's an open, you can pay the entry fee and take your lumps. :) I know that it is possible to play the champions of Bridge at certain tournaments.

Maybe the fun in a tournament is of a different kind than a side game for you. To me, on this site, the games all count about the same. It's harder to win a tournament than a single game. Perhaps that's the difference. When a prize is offered, that can make a difference too.