There's also someone reporting the same problem in this WineHQ thread: http://forum.winehq.org/viewtopic.php?t=4767&highlight=chessmaster. It doesn't provide any debugging information but the symptoms are exactly the same as I got. This user is on Gentoo. Two other people are also reporting similar behavior with Ubuntu (http://ubuntuforums.org/showthread.php?t=880854). Thus, it doesn't seems to be a bug specific to my system or configuration. This problem to be reproductible on many systems.
