• 1986: The Chessmaster series started with The Chessmaster 2000 by The Software Toolworks. It was published for Amiga, Apple II, Atari 8-bit, Atari ST, ZX Spectrum, Commodore 64, Amstrad CPC, MSX, Macintosh, and DOS; the game had a chess engine written by David Kittinger, and the manufacturer rated the game at 2000 Elo USCF, in reality it plays at approximately 1550-1600 Elo (1750-1800 USCF).
• 1988: Chessmaster 2100 was published for the Apple IIGS.
• 1989: Chessmaster 2100 was published for DOS.
• 1990 The Chessmaster was published for the NES.
• 1991: The Chessmaster was published for the SNES.
• 1991: Chessmaster 3000 was published for DOS, Windows 3.x.
• 1993: Chessmaster 4000 Turbo was published for Windows 3.x.
• 1995: Chessmaster 4000 was published for Windows 95.
• 1995: Chessmaster 3D for PlayStation had the Chessmaster 4000 engine.
• 1996: Chessmaster 5000 was published for Windows 95.
• 1997: Chessmaster 5500 was published for Windows 95.
• 1998: Chessmaster 6000 was published for Windows 95 and Windows 98.
• 1999: Chessmaster 7000 was published for Windows 98 and Chessmaster II was published for PlayStation.
• 2000: Chessmaster 8000 was published for Windows 98.
• 2002: Chessmaster 9000 was published for Windows
• 2004: Chessmaster 10th Edition was published for Windows XP.
• 30 October 2007: The current version, Chessmaster XI, was released for PC (titled Chessmaster: Grandmaster Edition) and Nintendo DS (titled Chessmaster: The Art of Learning), and 12 February 2008 for PlayStation Portable (also titled Chessmaster: The Art of Learning). It includes numerous tutorials by International Master Joshua Waitzkin for players of all skill levels.

The Chessmaster chess engine is called The King, written by Johan de Koning of the Netherlands. It was introduced in Chessmaster 4000; earlier releases featured a chess engine written by David Kittinger.

According to the September 2009 Swedish Chess Computer Association (SSDF) rating list, Chessmaster 9000 has an estimated Elo rating of 2718 on an Athlon-1200 PC. If multiple versions of other engines are stripped out of their list, Chessmaster 9000 ranks 14th among all engines tested. As of May 2008, Chessmaster 9000 remains the most recent version rated by the SSDF. Another rating list, CCRL, places Chessmaster 11th Edition in 24th place on its December 2009 list.

The King engine allows users to create new playing styles, also called "personalities", by manipulating several dozen different settings, such as King Safety, Pawn Weakness, Randomness, Mobility and others. Individual piece values can also be adjusted. Chessmaster 9000, for example, features over 150 different personalities ranging from International Grandmaster strength down to Stanley, who is described as a monkey and plays what are essentially random moves.

The personality feature has inspired many amateur computer chess enthusiasts to attempt to find more optimum personalities. In Chessmaster 10th Edition, the creation of new personalities has been made easier than before.

Notable games

• Larry Christiansen vs. Chessmaster 9000 (September 2002), annotated at GameKnot: Game 1, Game 2, Game 3, Game 4

Chessmaster won the four-game match against Christiansen held in September 2002, by a score of 2½-1½. The Chessmaster program was operated by John Merlino, the Project Manager of Chessmaster at the time of the match. Four different personalities were used in the match, the first three of which were based on famous human Grandmasters: Alexander Alekhine, Bobby Fischer, and Mikhail Botvinnik. The final game of the match used the default "Chessmaster" personality. Christiansen won the first game, lost the second and third games, and the fourth game resulted in a draw.

To date, various versions of Chessmaster have appeared on Amiga, Apple II, Apple IIGS, Atari 8-bit, Atari ST, Amstrad CPC, ZX Spectrum, Commodore 64, DOS, PC, Macintosh, Nintendo Entertainment System, Super Nintendo Entertainment System, Game Boy, Game Boy Color, Game Boy Advance, Nintendo DS, Sega Genesis (as a Sega Channel exclusive), Sega Game Gear, PlayStation, PlayStation 2, Xbox, and mobile phones. Early Macintosh versions Chessmaster 3000, 4000 and Multimedia were developed by Sebastian Rapport and Troy Heere that leveraged the Kittinger and de Koning engines respectively. Later Macintosh versions were ported by Feral Interactive , and the latest Macintosh version available is Chessmaster 9000. Ubisoft also offers a downloadable version of the game: "Chessmaster Challenge differs from Chessmaster 10th Edition in its simplified interface, and scaled-down tutorials. It’s a non-retail product available for trial and purchase through download only."

The more recent editions of Chessmaster include both 2D and 3D designs, and a large number of different boards and themed chess piece designs. The interface was revised for Chessmaster 10th Edition and features animated 3D sets in which the pieces "walk" between squares and have simulated battles when a piece is taken, reminiscent of Battle Chess or the Wizard's chess set from Harry Potter. (Previous editions also feature fully 3D sets but are not animated and the pieces do not battle.) Chessmaster 10th Edition also comes packed with a pair of red and blue glasses to view the set in "enhanced 3D".]

Xbox Live Arcade

An Xbox Live Arcade version with Xbox Live multiplayer and Xbox Live Vision camera support for the Xbox 360 called Chessmaster Live was released on 30 January 2008 for 800 Microsoft Points ($10 USD), but is no longer available.

This version of Chessmaster contained a bug allowing the white player to indefinitely hold up a match until a player resigned. The game was eventually patched so that neither player would gain or lose Elo points if they resign before the first move.

In Japan, Famitsu magazine scored the 1991 Super Famicom version of the game a 23 out of 40, and the 1994 Game Boy version a 21 out of 40.

Critical reaction to the Chessmaster series has been mostly positive. GameSpot commented that "Chessmaster has remained the consummate standard in console chess games since the '80s."IGN said that "the series itself remains the best way to play and learn about chess on the PC."

Chessmaster: Grandmaster Edition, the most recent PC edition of the series, scored positive reviews, with PC Gamer saying: "this one-stop shop for an entire chess-playing and learning family should last until you're all grandmasters."Chessmaster 10th Edition holds an 84% rating on review aggregator site Game Rankings. IGN gave Chessmaster 10th Edition a score of 8.4/10, calling it "the best chess game in town." GameSpot's review of Chessmaster 10th Edition said, "If you're looking for a good chess program that's packed with a plethora of features and all the bells and whistles, you'll be very happy with Chessmaster 10th Edition.

The mobile phone version of Chessmaster received a score of 9/10 from IGN, who called it "an absolutely superlative product that will be enjoyed for week after week by fans of the mental contest." IGN criticized the Nintendo DS version of Chessmaster: The Art of Learning for its lack of multiplayer, but gave it an overall positive review, with a score of 7.8/10. IGN criticized the "boring" presentation of the PlayStation Portable version of Chessmaster: The Art of Learning, but added that "there's no doubt that the information is valuable and can teach you the finer points of the game."

Although the Chessmaster engine is generally not as strong as the engines of other commercially-available chess programs such as Fritz, critics have praised the Chessmaster series for its comprehensive tutorials aimed at players of amateur and moderate skill levels. In its review of Chessmaster 9000, IGN said that "the series has always distinguished itself with first-rate chess teaching tools," and welcomed the game's "appeal towards inexperienced and mid-level players. With all manner of tutorials, detailed analysis and exercises, the game helps ease newbies into the experience." GameSpot's review of Chessmaster 10th Edition commented positively on the game's "huge bundle of features aimed at everyone from the neophyte who's looking to learn the basics to the advanced wood pusher who may need practice for tournament play."

A common criticism of the series has been the lack of new features in successive installments. IGN's review of Chessmaster 10th Edition commented, "it simply doesn't add enough over any of the last two versions to make it a necessary upgrade."

• List of chess software
• Computer chess