Oh cool, let me install this software, what, it won't install because it's missing quicktime? Oh it needs directx 8 runtime? That could be a problem. Let's advance the clock, 2004, that should be fine... What do you mean you can't run .NET 1.1 applications and so that won't run?

Ironically, wine is more likely to have a path to easily run those programs under Linux, but if you had a Linux binary from that era you'd likely have a hard time getting that to run, probably harder than the microsoft scenario. So old Windows software is more likely to run under Linux than old Linux software...