There's certainly a cutoff period for this. Post-DOS and pre-Windows XP. I can't remember, but I think a lot of it occurred with games that relied on DirectX versions that came out before DX9.
XP broke a lot of DOS games because it wasn't based on DOS the way Win95, Win98, WinME were.
Then later on Win7 broke some XP games because MS went hard and heavy on restructuring device driver APIs for power management and security reasons based on XP being the massive success it was, and those two things becoming much more important than they were when XP came out.
There's certainly a cutoff period for this. Post-DOS and pre-Windows XP. I can't remember, but I think a lot of it occurred with games that relied on DirectX versions that came out before DX9.
XP broke a lot of DOS games because it wasn't based on DOS the way Win95, Win98, WinME were.
Then later on Win7 broke some XP games because MS went hard and heavy on restructuring device driver APIs for power management and security reasons based on XP being the massive success it was, and those two things becoming much more important than they were when XP came out.