Boy, do I have memories about this game (which I still have, and it works, too!). It took me the longest time to figure out that the sample that sounded like "Illy galoob" was actually "illegal move"! It amazes me that I was playing chess when I was 7...but that's probably why I was always losing, heehee!
All I remember about this game is that it had samples. "The software tool works presents: The Chessmaster 2000" made the whole disk worthwhile.
O and a pre.. It works on Mono too!