I've actually found the opposite in my experience, though I would assume it's very much case-by-case. A recent example was Hyperbowl, a turn of the century game that broke on every version of Windows post-XP. Works fine on Linux with recent Proton and dgvoodoo2, though.

There's also DOSBox (which is quite capable at running win9x now, with Voodoo emulation) and 86box to fill those compatibility gaps too.