In fact I can play EarthSiege 2, a game from the 3.11/Win95 era, just fine on Win7 x64 with the only things not working being joystick input (I guess it does some shenanigans with the MIDI/joystick port in addition to using the windows joystick API) and the pause screen which shows your vehicle spinning around spins too fast (probably because its speed is tethered to CPU sppeed).
Microsoft takes, with the exception of drivers, a lot of effort to keep backwards compatibility. And that is why people like it, in contrast to Linux where "Things break" is the norm and even in OS X it's not unheard of. Oh, and also why big enterprises stay as far away as humanly possible from anything NodeJS or more modern than PHP and Java.
Enterprises want and need stability first.