Using a CD with Wine means navigating the disk from the Ubuntu desktop
using Nautilus and finding the appropriate installation file, usually setup.exe,
but not always. You can't always count of the CD to auto open as in Windows.

Wine also has different "bottles" to experiment with. I guess it is a play on
the name, Wine. There is the Win98 bottle, Win2000 bottle, etc. You may get
better results with using the appropriate one for your vintage programme. Good
luck in finding what you need.

What level of education are you involved in? I was a teacher for 30 years.