The 4th time

In 2026, the Chicago Cubs and the Chicago White Sox both clinched a spot in the postseason. And this is only the 4th time that both Chicago teams play October baseball. While reading the news about 2 Chicago teams in the playoffs, I’m just wondering about the results of these 4 postseasons.

So, the first time that both teams played in the postseason was in 1906. That was truly a long time ago. Back then, there was only the World Series. So, the Cubs and the White Sox met in the Fall Classic. This time, they played 6 games in the World Series. The White Sox got 4 wins and won the World Series title.

And the second time came a little bit late. The Cubs and the White Sox both clinched a postseason spot in 2008. The White Sox finished the season with 89 wins and 74 losses. They won the AL Central title. The Cubs won 97 games in 2008 and won the NL Central title. In the postseason, things didn’t go well. The Cubs were swept by the Dodgers in the NLDS. Meanwhile, the Tampa Bay Rays defeated the White Sox in the ALDS.

In addition, the third time was in the 2020 season. The 2020 season was a shortened one. In 2020, there were 8 postseason teams in each league. The White Sox finished the season with 35 wins and 25 losses. They were third in the AL Central. At the same time, the Chicago Cubs got 34 wins and lost 26 games in 2020. They won the NL Central title. Nonetheless, there were some problems for each team in the playoffs. The Miami Marlins defeated the Cubs in the NL Wild Card Series. Meanwhile, the White Sox and the Athletics played 3 games in the AL Wild Card Series. But the Athletics advanced to the next round.

This time, the Chicago Cubs finished the 2026 season with 89 wins and 73 losses. They were second in the NL Central and clinched a spot in the postseason. In the postseason, the Padres swept the Cubs in the Wild Card Series. And for the Chicago White Sox, they got 84 wins and 78 losses in the regular season. In the AL Wild Card Series, they swept the Astros to advance to the ALDS. In the ALDS, the Cleveland Guardians defeated the White Sox in 5 games.

Both the Cubs and the White Sox have rich history and well, famous curses. Interestingly, it’s only the 4th time that both teams play October baseball. The 1906 World Series was a long time ago. In 2008, the White Sox and the Cubs both lost in the Division Series. In 2020, they both fell short again and didn’t advance to the next round. In 2026, the Cubs didn’t play well in the NL Wild Card Series. But the White Sox beat the Astros in the AL Wild Card Series. However, the White Sox lost in the ALDS. Hence, a key thing is that it will probably take a while to see them meet in the World Series again.