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The OpenStudio-server project is on GitHub, so you could always just configure your server to do the same stuff that the docker stuff is doing. The entrypoint is the Dockerfile. You'll see it starts off with an image nrel/openstudio:xxx
(see NREL/docker-openstudio) which is based off an Ubuntu distro (14.04 currently).
Aside from heavily relying on Unix tools and having different paths, I think you might be able to do it on Windows Server (You can install Cygwin or the unix tools), but it'll probably be quite an annoying process though.
Disclaimer: I don't know the entire code base of OpenStudio-server, and I certainly have ZERO familiarity with Windows Server, so take everything I say with a big fat grain of salt.