The newest iteration in the Chessmaster series features an extensive Chess-tutorial by Chess Master Josh Waitzkin. Based on his book "The Art of Learning" and accompanied by the comments of Chess Grandmaster Larry Christiansen, beginners as well as advanced players can learn and perfect their skills in several dozens training sessions with extensive examples and explanations. The game also includes 900 famous chess plays to show off the skills of the masters and what lead to their victory.

To test his own skills, the player can choose to play against several AI-opponents that greatly differ in skill and used tactics or go online and play in ranked matches, tournaments and others. After each match the player can also choose to let the AI analyze the past match to show the bad and good moves of the play. By winning ranked plays, the player can also unlock new 2D and 3D chess sets including a 3D chess set featuring the rabbits from Rayman Raving Rabbids If the player doesn't want to play a full match, he can also try to solve the several hundred chess puzzle available.

Chessmaster: Grandmaster Edition also features several mini-games like "Pathfinder", which is kind of a Nibbles-clone with chess pieces, or "Fork My Fruit" in which the player uses the chess pieces and their corresponding moves to capture two or more fruits on the board at the same time to earn points.