Can't say I've tried to boot this on a modern PC in a long while.
That said, I did the other day. I was only able to make D2 classic boot while in windowed mode, and, the windowed mode could not be expanded at all. So, it was stuck running as a tiny af 800x600 pixel window IIRC. Far too small to actually play.
Is there an easy way to make it run maximized?