Chessmaster 5000 is the 10th Anniversary release of the game.
This implementation features a revised Windows interface, new tutorials, a new chess database with over twenty seven thousand entries, new time controls, sound effects and music.
The game can be played against an AI opponent, against another person or against a remote player.
The game's documentation lists the following as the top fifteen new features of this game;
New engine optimised for a 32-bit Pentium
New graphics including more than ten new chess sets both 2D and 3D plus a number of new boards
A new chess database with twenty seven thousand entries. This is not installed with the game, it stays on the CD-ROM
Over 20 new tutorial courses written by Eric Schller, the Californian State Champion
A new Windows 95 interface which makes use of pop-up menus and context sensitive help. Chessmaster 5000 also supports long file names
A NEW Coach window which shows a quick summary of all possible moves.
Custom True Type chess font which lets Chessmaster 5000 support figurine notation and embedded board diagrams in annotations.
Over sixty new opening books customised to simulate the play of a famous grand master.
Over thirty new personalities of all levels
New time controls including the Fischer time control, the hourglass time control and a new LCD-style digital clock in addition to the analog clocks.
Two thousand named opening variations, a great increase on earlier versions which recognised two hundred. Among the new openings are the hippopotamus, the tumbleweed gambit, and the Latvian Defence/Corkscrew counter gambit
A glossary with over sixteen hundred entries
Enhanced annotator now generates summary statistics for the game and additional commentary on inadvisable moves.