Ches sis just tough for this, I think. My DS5 is generally a good sport (he's a game addict), but he often cries when he loses at chess. He's not a snotty bad sport, but a weepy one. (Both are unpleasant, IMO.) He will be able to compete next year in K through school, and I'm wondering if he's really mature enough yet. To some extent, though, I think this may come with practice. I wonder if you have any coaches or chess...leagues (sorry, don't yet know the terminology) in the area where experienced adults could offer some advice? I wonder if playing some other kids at something less charged than a competition might be a better starting point? You don't want him to get turned off. I say this having seen a friend's (highly competitive) child compete recently in something different, lose, and declare that he never wants to enter something like that again.