In my experience, on Windows a lot of old stuff runs as long as you have whatever registry setting enabled that lets you run non 64 bit programs. This isn't available on every windows pc but if you're running it on your home pc, you can probably get it. A lot of old games don't work but old things that don't use graphics almost always run.

In wine, it's basically the same story. A lot of old stuff runs especially non graphical old stuff. Some old windows games don't work on wine but just because something old doesn't work on Windows doesn't necessarily mean it won't work on wine and vice versa.

I would rate wine as slightly more compatible with late 90s and early 2000s games than Windows is but ymmv. Graphics stuff tends to work a little more often on wine. Some mid 2000s games use obscure hacks that are impossible to ever get running on wine.