Chessmaster Challenge is a chess simulation game based on the Chessmaster series developed by the company Ubisoft. It features levels that range from easy to very difficult to accommodate first time, amateur, and expert chess players. As soon as this program is launched, there are three main options from which to choose: a comprehensive tutorial, a match against Artificial Intelligence, and chess puzzles. The tutorial features a voiceover that will narrate the instructions and tips to the user. The initial part of the tutorial discusses the basics of the game such as the moves for each piece. More complex chess moves like en passant and casting are discussed as well. The latter stages of the tutorial cover strategy and making intelligent moves against an opponent.
Every chapter in the tutorial features exercises, which the user can work on to apply what has been learned. Users can make actual moves on the board, and the program gives notification if the move is incorrect or potentially helpful to the opponent. In the actual chess matches, the player can select an opponent, color of the chess pieces, and game time. The selection features photos of the opponents including their respective rankings. Before the tutorial ends, it describes the kinds of game play in tournaments, as well as how to find tournaments in which to participate.