The Chessmaster is a game where the player has the chance to play against the CPU controlled Chessmaster at a standard game of chess. The ultimate goal is to outmaneuver your opponent and checkmate them.
To play the game, 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. There are 16 different difficulty levels, including beginner levels, standard levels and 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. The player can also use a teaching mode to see all the possible moves with the selected piece.
Gameplay is fast-paced and challenging, requiring strategy and skill to win. Players can compete against each other using two controllers, or play against the Chessmaster solo, either playing as white or black.
The Chessmaster was released for the Sega Game Gear in 1970, a platform known for its portability and impressive game lineup.