Checkers is a video game based on the board game checkers. It was made for the Atari 2600 by Activision. What's notable about this version of the game is that the screen turns black when the opponent AI is computing moves to make against you, and given how fast the Atari 2600 is, a regular game can take nearly an hour to play.

In this run, Winslinator decides to play the game at the "Game 1" difficulty. Since the lower difficulty gives the CPU much less time to think compared to the higher difficulties, Winslinator focuses on beating the it in the least amount of moves possible while also minimizing CPU thinking time.