I think the only game I ever had trouble running on a newer version of Windows was James Bond 007 Nightfire but compatibility mode seemed to work okay. I haven'

I think the only game I ever had trouble running on a newer version of Windows was James Bond 007 Nightfire but compatibility mode seemed to work okay. I haven't played heaps of games in the last decade but any issues have been more with getting the right version of the Visual C++ runtime or PhysX (which Steam usually handles for you anyway) rather than the underlying operating system.