Chessmaster Online (1996) - MobyGames

Chessmaster Online was a free on-line game based on Chessmaster 5000 which allowed chess players to play against each other and chat over the internet via MIndscape's servers. Alternatively the player could play themselves on their own machine.

The Chessmaster 3000 (1991) - MobyGames

Chessmaster 8000 (2000) - MobyGames

Chess Wars - DOS Longplay - Part 008 - FMV Black Queen Takes White

The Chessmaster 2000 (1986) - MobyGames

Chess Wars: A Medieval Fantasy (1996) - MobyGames

Windows Chess – Allvideo Classic Games

Millennium Chess Computer - King Exclusive Chess960 Fischer Random

Chessmaster 6000 (1998) - MobyGames

Chessmaster Online (1996) - MobyGames

hub-linux-ubuntu/install/overlay/var/lib/squidguard/db/hobby/games

Chessmaster - Chessprogramming wiki

Download Chessmaster 5500 (Windows) - My Abandonware

My Top 101 Old Skool Games

Missing Kelp Seeds :) - Off-A - Asexual Visibility and Education

The Chessmaster 3000 (1991) - MobyGames