9 games
78Chessmaster 2000
1986 · Amiga, Amstrad CPC +11

Chessmaster 2100
1988 · Amiga, Apple II +4

Chessmaster 3000
1991 · MS-DOS, Windows +1

Chessmaster 4000 Turbo
1993 · Windows, macOS
The Software Toolworks
80Chessmaster 6000
1998 · Windows, macOS

Chessmaster 9000
2002 · Windows, macOS
Xbox exclusive89Chessmaster 10th Edition
2004 · Windows, Xbox
50Chessmaster: The Art of Learning
2007 · Nintendo DS, PlayStation Portable +1
Ubisoft Sofia
Xbox exclusive80Chessmaster Live
2008 · Xbox 360
Ubisoft Sofia