That would depend on how the program talks to the GPIB. Does it use a custom driver? GPIB.SYS? The thing here is to check how the app talks to the GPIB and check that the board you buy comes with the DOS drivers (or they can be downloaded). CEC GPIB boards come with a full set of drivers.
BTW, Windows XP has had ALL 16 bit operations removed. DOS applications and old 16 bit Windows applications will not run. If you scrounge around the net, you can find some beta emulators that people are working on.
Rob