IIRC, there have been several instances of this between releases, less so from the user application perspective, but rather from the driver model.
Windows 3.1 to Windows 95 (16- to 32-bit), Windows ME to Windows 2000 (NT kernel), Windows XP to Vista (UAC etc.) each saw various issues with device drivers.
The extent of user application backwards-compatibility is impressive, with only Windows 10 removing 16-bit application support (boo). For example, even now it's possible to double-click on the application icon at the left-hand of the window title bar to close the application - à la Win 3.1.
> The only mistake Microsoft made was not doing rolling releases
I think they're 'fixing' that with Windows 10.