The lengthy Major League Baseball season has transitioned into a final sprint as September unfolds. Both the Chicago Cubs and White Sox clinched playoff spots on Thursday, marking only the fourth instance in MLB history when both teams entered the postseason simultaneously. Previous occurrences were in the years 1906, 2008, and 2020.
The Cubs’ Journey
The Chicago Cubs will end the regular season in second place in the National League Central. This marks their fourth consecutive season finishing in this position, as the Milwaukee Brewers claimed the division title once again. The Cubs, who secured a playoff berth last Thursday, are competing closely with other teams for the top NL wild-card spot.
Through Friday, the Cubs have a record of 88-73. However, their doubleheader against the Red Sox ended unfavorably, with losses of 4-3 and 2-0. With only one game left, scheduled on Sunday at 2:05 p.m. against the Red Sox in Tampa, Fla., the Cubs aim to solidify their playoff positioning.
Despite losses, the Cubs remain 1½ games behind the Padres, who suffered a defeat against the Diamondbacks on Friday. The Phillies trail the Cubs by half a game following their game loss to the Rays. The Cubs hold valuable tiebreakers over both the Padres and Phillies, making their playoff entry more likely.
In previous postseason appearances, the Cubs last reached the playoffs in 2025 as the No. 4 seed in the National League as the top wild card. Back then, they defeated the Padres 2-1 in the wild-card series but were later defeated by the Brewers in the division series 3-2.
The Cubs boast 22 postseason appearances throughout their history, achieving eight division titles, four wild-card berths, 17 pennants, and three championships in the years 1907, 1908, and 2016.
Remarkable Feats
A significant highlight for the Cubs includes Pete Crow-Armstrong’s rare achievement. He became the seventh player in MLB history to achieve 40 home runs and 40 stolen bases in a single season, with 45 home runs and 41 steals.
- Previous players achieving this feat include notable names like José Canseco in 1988, Barry Bonds in 1996, Alex Rodriguez in 1998, Alfonso Soriano in 2006, Ronald Acuna Jr. in 2023, and Shohei Ohtani in 2024.
The White Sox’s Journey
The White Sox celebrated their postseason clinch with a record of 83-77 through Friday. Their recent victory against the Rockies with a score of 6-1 enhances their competition for the American League Central crown. While trailing the Cleveland Guardians by a game, they maintain the potential to ascend to the top of the standings accompanied by a two-game schedule against the Rockies on Saturday and Sunday.
In the event of tying records with the Guardians, the Sox possess the tiebreaker advantage necessary for obtaining the division title. Presently holding the No. 3 spot in the AL wild card, they exhibit prospects of potentially dethroning the Guardians to claim the top divisional spot.
The White Sox’s last playoff appearance occurred in 2021 as the AL Central champions, however, concluding in a loss to the Astros in the division series. Their postseason record includes 11 series entries, with six division titles, one wild-card berth, six pennants awarded, and championships captured in 1906, 1917, and 2005.
Insights into the Playoff Format
The upcoming playoffs commence with the wild-card round, scheduled from Tuesday to Thursday, following a best-of-three format.
- Higher seeds host all games during the wild-card round.
- Postseason divisions proceed with traditional formats: Oct. 3-10 features the best-of-five division series, whereas the League Championship Series advances to a best-of-seven arrangement from Oct. 11-20. The grand World Series finalizes from Oct. 23-31, also held as a best-of-seven event.

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