I own a Windows 8.1 machine (I don't wanna to upgrade to broken Windows 10, in fact I am considering installing Windows 7 or Linux on this machine, because of all these issues).
But in my house there is also 2 Windows 10 laptops, and a bunch of other computers with varied other OSes.
Basically, no DirectDraw games work properly on Windows 8 and onwards, unless you use Wine (on Windows, yes).
For example SimCity 4 run extremely poorly on Windows 8 and 10, and recently after some driver updates it started to run buggy too (before it was only slow, now it is slow and renders stuff corrupted, with the interface randomly blinking in and out of existence,
particle effects disappearing, colour corruption, and so on).
But when I use Wine it works mostly fine.
The game Arcanum: Of Steamworks and Magick Obscura also doesn't work without Wine, it renders black rectangles everywhere and keeps crashing, but with Wine it works perfectly.
In fact I am using Wine so much that this is why I am considering dropping Windows entirely, I've been having more reliable experience Windows Gaming with Wine than with Windows itself.
Both SimCity4 and Arcanum I got from GOG.com and they both have all updates, I also tried them both modded and unmodded, it makes no difference, the only thing that makes a difference is Windows version (on the Windows 7 spare machine they work correctly
without workarounds) and if I am using Wine or not (using Wine, in any Windows version and any Linux version, both work correctly).