It should as it isn't running Windows app through wine but via a dedicated VM (managed by a docker container). Anything that can be ran in a qemu vm, should work fine.
Not sure on older versions... MS used to generate new evaluation ISOs every few months with a hard fuse in them... Can't speak for recently since it's been years since I've needed to test for old IE versions. If you choose to customise, I'd suggest going with one of the "lite" modified versions of Windows 10... since this will reduce the default surface a lot without the bridge to some of what Win11 added while jumping the shark.