I've been cursed with memories of this weird PC game I played ever since I was a kid. I made some mockups:
The main part of the game is this game board where you progress along the path and solve little word questions at each spot. The goal is the train tunnel at the end.
When you enter the tunnel, you are met with a disembodied face which mocks you for not solving enough questions correctly, and then he opens a trap door beneath you and you fall through the void and land back at the beginning of the board.
These memories are from forever ago but they're so clear. What the hell is this game?