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winning is the reward for the hard work put in at practice, a player should always be developing whether it is youth, high school, juniors, college or pros. A player and coach always wants to win - losing sucks. Winning produces positive development, it makes a player and coach work harder to keep winning and developing.
I think the other posters are missing something here. It always matters. I am not saying its life or death and i am not saying its win at all costs but winning and losing does matter at every age. If a team loses all the time the players get discouraged and a lot of them will quit. If they will all the time then the kids tend to get a little overzealous and the parents go nuts. A good balance of wins and losses not only makes the games more fun but will also drive the rights kids to work harder and that is where the development comes from. so , personally, it always matters.
now if you looking for an answer on when you think you kid will get looked at for some future advancement beyond HS then you may have to go back to Pee Wee's. Some kids start getting recruited and watched in middle school now. I thinks it is sad to have to do that but that is reality.
The kids should play, act and want to win but really too many coaches, teams and parents think too much about winning. The kids are fine with a good close game and being on a competitive team. With that said, being on a top competitive team especially in the bigger tournaments will get the kid more attention...if that's a goal.
Bantam, Midget, high school really.
Beatcuff - you have no idea what you are talking about. Players do get recruited and do commit to college as early as middle school.