I love Chessmaster, but cannot play it on my Windows 10 work computer. I do not have administrator rights. Thus, I cannot enable Directplay in the directx settings. Any possible workarounds?

i have administrator rights on my pc and i can not install directplay either. guess your only solution is to use an earlier system.

Same problem. I had to go to an old box running Win 7.... 9K remains one of my fav chess sims, but it does not seem to play nice with Win10 on a work machine (gotta love the admin priv!)...alternately, get dirt on youyr sys admin, and blackmail them for access (dirty evil chuckles in the background)

It is possible to install Chessmaster 9000 in Windows 8, you can even run it in windows 10.
But you have to be patient, the installation program of Chessmaster 9000 in windows 8 will pop up in 5 minutes or so, after clicking on setup.
You first have to uninstall the Windows Update KB3086255 on Windows 7/8/8.1
https://youtu.be/WmjFfgE5gDk
And enable DirectPlay in Windows 8/8.1/10
It is not possible to install Chessmaster 9000 in windows 10 but it is possible to run it in windows 10. If you have a legal copy.
You have to copy the folder Ubisoft in program files in windows 8 after you installed Chessmaster 9000.
Than in windows 10 you just past this folder in program files. You also have to copy the folder Chessmaster 9000 in the documents folder in windows 8, to the documents folder in windows 10.

Chessmaster 9000 runs perfect on my windows 10 64 bit PC.