Heh, I'm not that good at Chess...

It depends. If it's an older Chessmaster (4000 or less) I could usually, if it's 10th edition, it would be seldom that I win. There's some other computer programs that blow Chessmaster out of the water, though, in playing strength. Fritz, probably the second-best selling commercial chess program beat the current world champion in a 6-game match.

Hydra, a dedicated computer, has never lost to a human.