There are a good few posts here on getting Windows 95/XP etc running on the Pi.
Thought I'd spend some time messing around and got Windows 1.01, 2.1, 2.11, 3.1, 95 working on the Pi under qemu.
Windows 1.01
https://www.youtube.com/watch?v=3cGdPwgmATc
Windows 2.1
https://www.youtube.com/watch?v=ry6Ri4H6HW4
Windows 2.11
https://www.youtube.com/watch?v=aMar8In2ZAo
Windows for Workgroups 3.1
https://www.youtube.com/watch?v=glwDvL8bxrQ
Windows 95
https://www.youtube.com/watch?v=glwDvL8bxrQ
A quick write up on the process I followed:
http://blog.gjmccarthy.co.uk/?p=386
Then for the next thing I got Netware 3.12 working on the Pi with bochs.
For all the other old timers out there - remember the Netware snake. Yes - it works on the Pi. (Near the end of the video)
Its hardly usable though and I didnt try get any of the network drivers working, but it was still fun.
https://www.youtube.com/watch?v=9iwtg8NpM48
http://blog.gjmccarthy.co.uk/?p=402