The thing is, this hasn't been true for a long time. At this point Wine/dosbox are far more compatible with old weird software than the current version of windows. For example, you can't run 16bit Windows programs at all on Windows.
You even have projects like otvdvm, running wine on windows to support older programs (or dosbox, which I think everyone is a lot more familiar with). http://www.columbia.edu/~em36/otvdm.html
The genuine article tends to be better while older platforms are supported, but at some point, inevitably, older platforms are dropped because supporting them costs money. When that happens, open source imitations end up with better support than the original.