How to play The Chessmaster on Mac

Game summary

The Chessmaster is a game where the player has the chance to play against the CPU controlled Chessmaster at a standard game of chess. To play the game the player must pick up the chess pieces with there hand cursor and place it in the desired location, within the rules a standard chess game. There are 16 different difficulty levels that includes 2 beginner levels, 13 standard levels (ranging from an average of 5 seconds to 4.5 minutes per shot depending on level), and a infinite level that will keep thinking of a shot until a perfect shot can be made or it is forced to move. There is also a teaching mode that shows the player all the possible moves with the selected piece. Two players can play each other with two controllers and there is also an option of letting the Chessmaster play itself.
First released: Dec 1991

Play The Chessmaster on Mac with Parallels (virtualized)

The easiest way to play The Chessmaster on a Mac is through Parallels, which allows you to virtualize a Windows machine on Macs. The setup is very easy and it works for Apple Silicon Macs as well as for older Intel-based Macs.

Parallels supports the latest version of DirectX and OpenGL, allowing you to play the latest PC games on any Mac. The latest version of DirectX is up to 20% faster.

Our favorite feature of Parallels Desktop is that when you turn off your virtual machine, all the unused disk space gets returned to your main OS, thus minimizing resource waste (which used to be a problem with virtualization).

The Chessmaster installation steps for Mac

Step 1
Go to Parallels.com and download the latest version of the software.
Step 2
Follow the installation process and make sure you allow Parallels in your Mac’s security preferences (it will prompt you to do so).
Step 3
When prompted, download and install Windows 10. The download is around 5.7GB. Make sure you give it all the permissions that it asks for.
Step 4
Once Windows is done installing, you are ready to go. All that’s left to do is install The Chessmaster like you would on any PC.
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