why not make a virtual with windows 95 and see what it does?
It's likely that wont help, as the "hardware" being used by the virtual machine when running an older OS often isn't up to the task of running games, even older ones. One of my old games, Warlords III (1998), can't run on XP or later, so I tried using a virtual machine of windows 95 and 98 to run Warlords III, and it ran into a whole NEW slew of issues due to the VM's imaginary hardware.