The Major League Baseball season has entered its final stages, and both the Chicago Cubs and the Chicago White Sox have secured spots in the playoffs. This marks only the fourth occasion in MLB history when both teams have entered the postseason together, with previous instances in 1906, 2008, and 2020.
Cubs’ Prospects
The Cubs will finish in second place in the National League Central for the fourth consecutive year, as the Milwaukee Brewers have claimed their fourth straight division title. Cubs manager Craig Counsell celebrated the achievement with his team at Wrigley Field after securing their playoff spot on September 24, 2026.
The Cubs’ record stood at 88-73 through Friday. However, their doubleheader against the Red Sox saw them losing both games 4-3 and 2-0. With one game remaining against the Red Sox in Tampa, Florida, the Cubs are 1.5 games behind the Padres for the top wild card position. The Cubs have tiebreakers against both the Padres and Phillies.
The Cubs made their last playoff appearance in 2025 as the No. 4 seed, emerging victorious over the Padres in the wild card series before being eliminated by the Brewers in the division series. In their postseason history spanning 150 seasons, the Cubs have made 22 appearances, earned eight division titles, four wild-card berths, 17 pennants, and three championships.
Significantly, Pete Crow-Armstrong became only the seventh player in MLB history to achieve 40 home runs and 40 stolen bases in a season, joining names like José Canseco in 1988 and Shohei Ohtani in 2024.
White Sox’s Journey
The White Sox are competing closely with the Cleveland Guardians for the American League Central title. After securing a playoff spot on September 24, 2026, in Kansas City, Missouri, the White Sox find themselves trailing the Guardians by one game following the Guardians’ victory over the Royals.
The White Sox possess a record of 83-77 with two games remaining, both against the Rockies at their home field. If they tie with the Guardians, the White Sox hold the advantage through tiebreakers and could win the division title.
Their last playoff appearance was in 2021 as the AL Central champions. In their 125 seasons, the team has made 11 postseason appearances, capturing six division titles, one wild-card berth, six pennants, and three championships.
Playoff Structure
The playoff structure includes multiple stages:
- Wild-card round (Best of three): Takes place from Tuesday to Thursday, with all games hosted by the higher-seed team.
- Division series (Best of five): Scheduled from October 3-10 in a 2-2-1 format.
- League Championship Series (Best of seven): Occurs between October 11-20 in a 2-3-2 format.
- World Series (Best of seven): Held from October 23-31 in a 2-3-2 format.