Chessmaster is a game where the player has the chance to play against the CPU controlled Chessmaster at a standard game of chess. To make a move, the player must pick up the chess pieces with their hand cursor and place it in the desired location, within the rules of a standard chess game.
The gameplay offers 16 different difficulty levels, including two beginner levels and thirteen standard levels, ranging from an average of five seconds to four minutes per shot depending on level. There is also an infinite level that will keep thinking of a shot until a perfect shot can be made or it is forced to make a move. Additionally, the game features a teaching mode that shows the player all possible moves with the selected piece.
The game supports two-player gameplay using two controllers, and there is also an option for letting the Chessmaster play against itself. The game's AI adjusts difficulty levels according to performance, making it suitable for players of various skill levels.