if I think I understand your point I would recommend:
Viper racing (1998) --- great racing game for the PC. Sort of like a poor man's version of the granturismo series on the PS, but the career mode and game overall is quite limited --- I still go back and play through it on ocassion though -- but I think you will need a Win 98 legacy box (mostly due to sound issues). Also, has some of the best force feedback I have ever seen (I mean felt) in a PC game.
I would also point out "Supreme Snow Boarding" (~ 2001) known as "Boarder Zone" in the USA --- great little game with great physics --- reminds me of 1080 snowboarding on the Gamecube (or was that the N64?). There is a guy still supporting this game (with an aftermarket patch) so it has improved compatibility with Vista/Win 7.