I spent ages getting wipeout 2097 to work on xp....
Nowadays I usually use a virtual install of the relevent version of dos/windows to get the odd old game that I play.
Which means I have a copy of DOS 6.2 - Win 3.1 - Win 95b - Win 98 - Win ME and Windows 2000 on my main system upstairs as well as XP.
If I can't get my old game to play in one of those then there's not much hope