I have had very bad success rate with my old Windows CDROM/DVD era games. Pretty much all of them either have some kind of DRM or they run but with bugs.
When available I just buy the GOG versions instead, but even those versions sadly often have issues.
Meanwhile slightly older games from the DOS era works perfectly everywhere thanks to DOSBox. I would love to see something like that for old Windows. Merge DOSBox with WINE, someone?
You can run Windows 95 in DOSBox. You could also just run WINE which runs most old games.
You can use WineD3D for Windows.
Usually dgVoodoo handles most of the games (that don't have actual bugs like this game) fairly well.
Otherwise, 86Box is a pretty good full-system emulator for everything up to the early 3D era.
As for DRM, there's various ways around it of course :)