Both Chicago teams are headed to October for just the fourth time in history. Here’s how the previous three trips played out and what could make 2026 different for White Sox and Cubs.
Just minutes after the Chicago White Sox beat the Kansas City Royals 9-1 on Thursday afternoon to clinch their first postseason berth since 2021, the Chicago Cubs secured a playoff spot of their own across town.
Ryan Zeferjahn recorded the save in a 2-1 win over the Miami Marlins at Wrigley Field. With that, the Cubs are headed to the National League Wild Card Series, though whether they’ll host it remains to be seen.
The White Sox still have more to play for. With three games against the Colorado Rockies remaining this weekend, they have a chance to win the AL Central and earn a first-round bye straight to the Division Series.
For just the fourth time in history, both Chicago teams will play postseason baseball in the same year. The timing invites comparisons between them, but the question now is whether either team can turn a playoff berth into something more.
2020 Wild Card Defeats
The last time both teams made it was 2020, a season that came with a significant caveat. The COVID-19 pandemic shortened the schedule to 60 games, and an expanded playoff field allowed eight teams from each league to qualify.
The White Sox finished 35-25, one game behind the Minnesota Twins in the AL Central, before losing a three-game Wild Card Series to the Oakland Athletics.
The Cubs won the NL Central at 34-26, only to be swept at home by the Marlins in two games. Both teams were in the postseason, but neither was there for long, and fans couldn’t attend those Wild Card Series.
For a closer comparison to this year, go back to 2008.
2008 Division Series Letdown
The White Sox finished their scheduled 162 games at 88-74, tied with the Twins atop the AL Central. They won a 1-0 tiebreaker game to claim the division and return to the playoffs for the first time since their 2005 World Series championship.
On the North Side, the Cubs went 97-64 in their second season under manager Lou Piniella. They won the NL Central and entered October with higher expectations than the White Sox, but the Los Angeles Dodgers swept them in the Division Series.
The White Sox lasted one game longer, losing the ALDS 3-1 to the eventual American League champion Tampa Bay Rays. (Chicago Cubs)
1906 World Series Matchup
That leaves 1906, when there were no playoff rounds before the World Series. The American League and National League champions went straight to a best-of-seven matchup, and both of them came from Chicago.
The Cubs went 116-36, posting one of the greatest regular-season records in baseball history. The White Sox finished 93-58 and beat them in six games anyway, claiming the first World Series title won by a Chicago team. (MLB.com)
So while both teams have reached the postseason together three times before, neither advanced past its opening series in 2008 or 2020. In 1906, their opening series was the World Series.
The 2026 Cubs and White Sox have taken different paths to this point, and there’s something especially easy to root for about this underdog White Sox team. Chicago’s South Siders may finish with a worse record than the Cubs, but 1906 is a reminder that the better regular-season record doesn’t settle anything in October. The White Sox have a chance to become the talk of the town with a deeper playoff run.
Their best path starts this weekend. Win the AL Central, and the White Sox go straight to the Division Series. The Cubs will have to earn their way there through the Wild Card Series.
