So I knocked the dust off my copy of Chessmaster 9000 and I'm having troubles installing it on Windows 10. The disk doesn't open automatically, so I'm clicking on the folder and trying "setup", "autoplay" and "autorun". This opens a window and I'm hitting "install" and then nothing happens. I tried running all three as administrator and that didn't work either.

Are they just incompatible at this point? Any help would be great.

Thanks

Do you mean you try to install from the CD?
Although you can install under Windows 10, the game won't run due to lag of safedisc and securom support.
There are reports on this issue on the web, using key word "windows 10" & "safedisc" you can found lots page talking about it.
I suffer from the same problem when I try Civ 4.