The Ultimate Chess Challenge is a handheld chess game that utilizes the core mechanics of Chessmaster 2100. This includes standard tactics like en passant, castling, check, and checkmate. The game also features draw conditions for various reasons. Players can choose to set move time limits and specify the CPU's thinking time.
The gameplay is centered around playing chess against both the computer and other human opponents. When playing against the computer, players can press the B button to receive a hint, although it is not guaranteed that the computer will provide one. This handheld game offers a unique experience for fans of chess on-the-go.