[9] Included with the purchase of 5500 was a copy and free subscription to Chessmaster Live, an online game that was also available separately on the chessmaster.com website.

In a 1995 comparison between 11 chess programs, Computer Gaming World rated a pre-release version of Chessmaster 5000 the highest.

[15] Computer Games Strategy Plus criticized the lack of PGN support and described the database as "broken".

The game was summarized: "If you just want a good chess playing program with lots of eye candy, Chessmaster 5000 will suit you fine.

"[12] Computer Games Strategy Plus gave a more positive review for Chessmaster 5500, which was said to fix bugs from the previous version although a few issues still remained.