If I were to guess, I'd try to run qemu-kvm with exposed VNC... a "builder" intermediate that installs w95 as a base image, with a second dockerfile using that as base and installs the game in the virtual disk using overlay images.

That should be decently fast, the only thing I dunno is how easy it is to automate a w95 install when you only have an 1:1 iso image of a retail setup CD/diskette.