You played 2 months ago on the same machine using Win10 ?
If so, did you install a Windows update, or make other changes around the time the game stopped running ?
- If you have not played the game on Win10 and have the disc based version the problem would be because of a DRM Blocking
feature MS built into Win10. I have more details in my post at ---this thread---
To make the disc based version of the game run you will need a noCD fix/hack from... games/midtown-madness-2
btw - Win10 has DX9/10/11 &12 (one DX8 file too). When you enabled Direct Play it made it possible to run DX7/8 games.