Last Time the Chicago Cubs Won a MLB Playoff Series

Chicago Cubs' Michael Busch (29) is greeted by Moisés Ballesteros as he returns to the dugout after scoring on a sacrifice fly by Ian Happ off Pittsburgh Pirates pitcher Paul Skenes during the second inning of a baseball game in Pittsburgh, Tuesday, Sept. 16, 2025.
(AP Photo/Gene J. Puskar)

The Chicago Cubs last won a playoff series in 2017. They defeated the Washington Nationals in five games during the National League Division Series.

Chicago then fell to the Los Angeles Dodgers in a 4-1 loss during the NLCS.

Last Time the Chicago Cubs Won an NL Pennant

The Cubs last won the pennant in 2016, recording a 4-2 series victory over the Dodgers to reach the World Series.

Chicago has clinched 17 pennants in franchise history.

Last Time the Chicago Cubs Won the World Series

The Cubs last won the World Series in 2016, winning a thrilling seven-game series against the Cleveland Indians.

It marked the team’s first World Series since 1908. The Cubs won back-to-back championships in 1907 and 1908.

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About the Author Read More @ShaneThurston25

Shane Thurston is a Web Content Writer for BetMGM, covering MLB and NBA. After graduating from the University of Kansas, his previous stops include MLB.com, Lawrence Journal-World, Manhattan Mercury, Bet Chicago Sports, WynnBET, and Sportsbook Review.

Shane Thurston is a Web Content Writer for BetMGM, covering MLB and NBA. After graduating from the University of Kansas, his previous stops include MLB.com, Lawrence Journal-World, Manhattan Mercury, Bet Chicago Sports, WynnBET, and Sportsbook Review.