As with the other games in this series there are many features available to the player. In addition to the many different chess boards, viewpoints and chess sets there are features that analyse the player's game, tutorials, a database of over two thousand named game openings. and an Opening Book Editor.
The main new features in this release of the game is the audio feature. The game has something called Illustrated Voice Analysis which
Analyses the game and provides feedback using ghosted pieces, arrows and the like. All of the game openings, the first three tutorials, and all of the in game dialogue boxes have been given the audio treatment.
John Waitzkin, then a twenty year old International Chess Master, joined the Chessmaster team for this release and the product includes five of his voice annotated games.
Finally there are some new sets of chessmen including a Staunton Brushed Metal set and a 3D Isle of Lewis set.
Installation of many of the features, e.g. the tutorials, remained optional to minimise the space used on the player's machine. These features were still available to the player but, as they remained on the CD and were not on the hard drive there was a performance hit. The game also featured on-line play but when tested in 2013 this service was no longer functioning.
The CM 5500 fully supported the TASC SmartBoard, an analog/physical chessboard with LEDs and sensors under each piece to identify them, so you could more easily set up a game. The device was connected through the parallel port, and the required drivers do not work under WinXP.