How many times have the Cubs and White Sox played a playoff game on the same day?

Both the Chicago Cubs and Chicago White Sox qualified for the 2026 MLB postseason as Wild Card teams. On Tuesday, both clubs will play Game 1 of their respective series on the road, with the Cubs visiting the San Diego Padres and the White Sox facing the Houston Astros. According to MLB Network's Jon Morosi, this marks only the ninth time in history that both Chicago franchises play a playoff game on the same day.

The first six instances occurred during the 1906 World Series when the two cross-town rivals faced each other. The occurrence happened only twice more over the next century, taking place on October 2, 2008, and September 30, 2020. The 2026 postseason appearance caps a major turnaround for the White Sox, who won 84 games following a 41-win season in 2024 and a 60-win campaign in 2025.