How to run NASCAR SimRacing on a Modern OS

Run setup.exe. If the installer doesn’t appear to run, check its wait chain, otherwise NASCAR SimRacing will install version 1.0 directly from the CD without a problem. CD 2 should be inserted into a drive when asked for. Do not install GameSpy. If your version of Windows 10 is up-to-date then the first time you run NASCAR SimRacing it will automatically run the Program Compatibility Assistant and will apply some settings that won’t work on the 3D configuration utility, but let it run anyway.

Open the config.ini file it created with notepad and edit this one line:
WINDOWEDMODE=1
Save the file.

Replace the 3DSetup.exe file with the 3D configuration utility from F1 Challenge 99-02 which you can download here. Just drop the new 3DSetup.exe into your NASCAR SimRacing folder and right-click it. Go to the compatibility tab for your new 3DSetup.exe and select Windows 7. Run it, click next (do not select a resolution), next and analyze. Then click finish.

Run the 3DSetup.exe again. Click Advanced and uncheck run benchmark. Click next, select your resolution, click next, and finish.

Run the NASCAR SimRacing.exe file and it will again run the 3D tool. Click Advanced and uncheck run benchmark. Click next, select your resolution, click next, and finish. The game will now launch. And yes, you need to do that last step each time you run it.