This has been my experience as well. Quite a few old games have become buggy or simply unplayable under recent Windows versions, but play fine under Wine. The most common symptom is the game becoming extremely slow on more modern DirectX iterations, which can ironically often be solved by using Wine DLLs.

There was one very ironic case with an old (1999) game that has been having issues on Win10. A long time ago, I used to run this game on Linux with Wine, and ran into a very similar issue back then, so I made a patch for the game. So I figured I'd try the same patch on Win10, and what do you know - it works.

The amusing part is that I don't remember what the patch actually does. I mean, it replaces a bunch of opcodes with NOP, but I have no idea what. I vaguely recall spending a day in IDA Pro to find those bytes, but nothing about the details.

The really amusing part is that game developers haven't figured out what the problem is, either, and so my who-knows-what-it-does patch is a semi-officially blessed solution for now:

https://steamcommunity.com/app/61500/discussions/0/215439774...

Such a good series. I didn't really _feel_ it with the third, though.

Funnily, when I was trying to get a 16-bit game to run, my final (and easiest) solution was to SSH to a linux machine, run it under wine, and do X tunneling back to my Windows system.

Works like charm.

DOSBox with Win 3.11 usually works well for these cases.

From what I understand, Microsoft could have totally kept 16bit application compatibility in 64bit Windows, but didn't for some reason. Apparently someone out there even compiled a version of NTVDM that works on Win 10 64-bit using leaked code or something.