No solid idea what the problem might be. Have you tried installing it in Windows 7 using the XP compatibility mode?
Also, you might check to ensure that Win 7 is using DirectX ver 7 or later. (Should be using ver 11 or 11a.)
https://support.microsoft.com/en-us/help/15061/windows-which-version-directx
Hi EscherehcsE, thanks for the reply. I checked and found my DirectX ver at 11. I'll try the compatibility checks again too. I don't even mind purchasing it again but can't find the real deal any where on the internet for years. I don't think it makes a difference that my XP was a 32bit system and my Win7 is a 64bit system. I 'll keep trying. Thanks for the help, any further input is welcome and appreciated. Sincerely, Bob
Well, I have some news, but it's not good. I downloaded the 60-minute trial version of Chessmaster Challenge, and I also duplicated your problem on my Win 7 box. However, I wasn't able to find a fix for the problem.
It seems your only options might be either buying a copy of Chessmaster 10th Edition on eBay or installing something like VirtualBox so that you could install Win XP into VirtualBox. I haven't done anything like the latter option, so I don't know how difficult it would be to do.
Does Chessmaster 10th Edition have the same extended tutorials?
Does Chessmaster 10th Edition have the same extended tutorials?
As far as I can tell, the tutorials in Chessmaster Challenge consist of the 29 Beginning tutorials in the "Chessmaster Series" tutorials in CM10. CM10 also includes some Intermediate and Advanced tutorials in the "Chessmaster Series". Also, CM10 includes some "Josh Waitzkin's Academy" tutorials and some "Larry Christiansen Attacking Chess" tutorials.
Before I give up completely on Chessmaster Challenge, I have one more idea to try with the installation. Give me an hour or two to try it out.
OK, my last idea didn't work, so I officially give up on Chessmaster Challenge. 
Hmm, it looks like the Chessmaster 10 forums have been shut down. If you do get a copy of CM10, you'll want to download and install (as administrator) the three patches for the U.S. version. Install the patches in order: the 1.01 patch, then the 1.02 patch, and finally the 1.03 patch.
One of the patches will allow you to start up Chessmaster without having to insert the CD/DVD into the DVD drive. You can get the patches here:
https://web.archive.org/web/20111214042822/http://forums.ubi.com:80/eve/forums/a/tpc/f/760105752/m/5081052236
Oops, the CM10 forums are still up; They just changed the link for some reason.
http://forums.ubi.com/showthread.php/397550-Chessmaster-10th-Edition-Downloads
Some years ago I purchased this game on CD and installed it on my XP desk top. It is the "FULL VERSION", it works great And I really like the tutorials in the learn mode. No matter how I try to install it on my Win7 lap top it won't include all the tutorials but functions normal in all other respects. I find the tutorials great as a refresher to sharpen up after not playing for long periods. Has anyone had and found a resolution for this issue or know where I can the FULL VERSION that will install on a Win7 laptop?
Thnks, Bob G