The Major League Baseball season has reached its crucial stage as September races to a close. Both the Chicago Cubs and White Sox find themselves in pivotal playoff hunts. The Cubs are set to finish second in the National League Central, marking their fourth consecutive season in this position. The Milwaukee Brewers have clinched their fourth straight division title. Meanwhile, the White Sox are locked in a tight competition with the Cleveland Guardians for the American League Central lead. A win for the Sox would signify a striking turnaround after enduring three consecutive seasons with over 100 losses.
The playoff picture is ever-evolving, and staying updated is essential for avid baseball fans. Subscriptions to the Chicago Tribune offer comprehensive coverage, including insider newsletters for the Cubs and White Sox.
Cubs Update
The Cubs are having a strong finish, with left fielder Ian Happ marking a milestone with a double during a recent victory against the Cincinnati Reds. On Sunday, September 20, 2026, the Cubs secured a commanding 9-1 win against the Reds in Cincinnati.
Record: 87-69.
Magic Number: 1 – This represents the combined number of Cubs wins and Arizona Diamondbacks losses needed to secure a wild-card spot.
Games Remaining: 6.
Wild Card Standings: The Cubs are half a game ahead of the San Diego Padres for the top wild card position and a full game ahead of the Philadelphia Phillies.
The Cubs are looking forward to a wild-card spot, having last appeared in the 2025 playoffs. They entered as the No. 4 seed, successfully defeating the Padres before losing a close series to the Brewers.
Historical Performance: 22 playoff appearances across 150 seasons, with several accolades including three championships in 1907, 1908, and 2016.
40-40 Club Watch: Pete Crow-Armstrong is on track to make history by achieving 40 home runs and stolen bases this season. Historical accomplishments include players like José Canseco and Barry Bonds setting impressive records in past seasons.
White Sox Update
Third baseman Miguel Vargas brought vitality to the White Sox during their recent win against the Detroit Tigers. On Saturday, September 19, 2026, the Sox claimed a 3-1 victory.
Record: 79-76.
Magic Number: 5 – The combination of White Sox wins and losses by the Houston Astros or Toronto Blue Jays needed to clinch a wild-card spot.
Games Remaining: 7.
The White Sox are narrowing the gap, trailing the Guardians by one game but owning the tiebreaker. The race for wild card positioning sees the Sox on top, 2½ games ahead of Houston and 3 games ahead of Toronto.
The Sox last made the playoffs in 2021 as AL Central champions. Historical stats reveal they have 11 playoff appearances in 125 seasons, with three championship titles.
Playoff Structure
The postseason kicks off with the wild-card round held from Sept. 29 to Oct. 1. This best-of-three series occurs entirely at the higher seed’s venue. The division series follows with matches from Oct. 3 to 10, using a 2-2-1 format.
League Championship Series runs from Oct. 11 to 20 with a 2-3-2 format, culminating in the World Series, slated for Oct. 23 to 31.
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