My son learned that lesson this year. He had been on a baseball team for three years that constantly won regular games and tournaments. It got to the point that when they lost the boys would act like a bunch of babies and cry and get unsportsman about it. I moved him off that team and we went to a new league. His team this year only won 4 games. He has now learned humility and that you can't always win but that if you play your hardest and do your best you're a winner. His team was great and even when they lost the boys would cheer for each other and be encouraging. They never blamed one another for mistakes or losses.

you have to show them that they won't always win, that even if you are winning, you can't gloat about it...teaching children humility and being a good sport has been lost. my nephew is the same way, and he's 6. if he isn't winning, he quits. trying to teach him not to quit and to stick with it is hard thing to do. he wants to come back to the game when he sees the rest of us having fun, but we tell him no, you quit. he'll learn, but learning to lose as a good sport isn't easy. kids these days have been taught that everybody can play and everybody wins and everybody gets a trophy. well, you know what? not everyone wins, not everyone is good at everything and sometimes you just have to accept that this isn't for you and find what you ARE good at...

is a debatable topic. either u let him win, to boost confidence, or teach the lesson that can't win them all. I'll go for the second option. u have to teach kids and prepare them for the future, that is not going to be easy out there.