It's possible that older compilers will have timing issues considering that newer CPUs are magnitudes faster than the CPUs such compilers were originally made for, like if you're using something for a 286. I've only had the problem once, and I can't even remember the compiler I was using. Anyway, my old DOS Turbo C++ compiler runs fine under command line in Windows XP as does Turbo Pascal and QBasic. If the compiler is actually old enough that it had specific DOS optimizations that won't work under the good ol command line, chances are someone in the Open Source Community has written a compiler for it to work in modern operating systems.
We can help you more if you tell us exactly what languages you are interested in.