I’ve tried getting Windows XP games to run both in windows 7/10/11 and wine with little success. However, I have gotten them to work in Windows XP virtual machines.

[–] Redkey@programming.dev 1 points 3 hours ago

The problem I find with many games made for Win95/98/XP is that the game uses one or more third-party libraries that were only "valid" for a year or two. After that, updates to the OS closed loopholes that the poorly-written old versions of the libraries relied on, but the poorly-written newer versions of the libraries released to deal with those issues then break compatibility with the previously-released game, which was never updated or patched.