From the Greatest Generation podcast wiki:

Starting with season two of Star Trek: Deep Space 9, Ben and Adam decided to change things up by employing a Chutes/Snakes and Ladders style board game with various “traps” resulting in possible podcast themes. At the end of each episode, the virtual die is rolled, and Ben and Adam advance as many spaces on the board, resulting in either a blank tile or an action tile to be carried out in the next episode’s review. The original board ran from episodes 197-227, when they completed the run at space 100. A new board was designed starting on episode 228, which added some new spaces and changed the layout, and it ran until episode 258. A new reset began on episode 259, which added three new squares, which replaced a Traveler, Quark’s Bar, and Banger space on the board.

These are the special squares I drew for the game!