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.
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.