After their back-to-back world championships in 1907 and 1908, the Cubs did not win another postseason series of any kind until 2003, and, of course, they didn't win the World Series again until 2016.
The Cubs won seven more pennants in the first half of the 20th century (and narrowly missed several more), but never captured the ultimate prize. They came closest in 1945, when they lost a seven-game Series to the Detroit Tigers and then disappeared from all postseason play for 39 years and from the Fall Classic for 71 years.
Lou Piniella's 2007 and 2008 teams were the first Cubs to make back-to-back postseason appearances since Frank Chance's legendary teams exactly a century earlier. Alas, Piniella's Cubs failed to win a single playoff game.
Below is the complete list of Cubs teams in the postseason.
1885
W. 87 L. 25 .777
Manager: Cap Anson
Best Player: John Clarkson
Finished first in National League
Tied St. Louis Browns 3 games to 3 in World Series
1886
W. 90 L. 34 .726
Manager: Cap Anson
Best Player: King Kelly
Finished first in National League
Lost to St. Louis Browns 4 games to 2 in World Series
1906
W. 116 L. 36 .763
Manager: Frank Chance
Best Player: Mordecai Brown
Finished first in National League
Lost to White Sox 4 games to 2 in World Series
1907
W. 107 L. 45 .704
Manager: Frank Chance
Best Player: Orval Overall
Finished first in National League
Defeated Detroit Tigers 4 games to 0 in World Series 1908
W. 99 L. 55 .643
Manager: Frank Chance
Best Player: Mordecai Brown
Finished first in National League
Defeated Detroit Tigers 4 games to 2 in World Series1910
W. 104 L. 50 .675
Manager: Frank Chance
Best Player: Solly Hofman
Finished first in National League
Lost to Philadelphia Athletics 4 games to 1 in World Series1918
W. 84 L. 45 .651
Manager: Fred Mitchell
Best Player: Hippo Vaughn
Finished first in National League
Lost to Boston Red Sox 4 games to 2 in World Series1929
W. 98 L. 54 .645
Manager: Joe McCarthy
Best Player: Rogers Hornsby
Finished first in National League
Lost to Philadelphia Athletics 4 games to 1 in World Series1932
W. 90 L. 64 .584
Managers: Rogers Hornsby, Charlie Grimm
Best Player: Lon Warneke
Finished first in National League
Lost to New York Yankees 4 games to 0 in World Series 1935
W. 100 L. 54 .649
Manager: Charlie Grimm
Best Player: Billy Herman
Finished first in National League
Lost to Detroit Tigers 4 games to 2 in World Series1938
W. 89 L. 63 .581
Managers: Charlie Grimm, Gabby Hartnett
Best Player: Bill Lee
Finished first in National League
Lost to New York Yankees 4 games to 0 in World Series 1945
W. 98 L. 56 .636
Manager: Charlie Grimm
Best Player: Stan Hack
Finished first in National League
Lost to Detroit Tigers 4 games to 3 in World Series1984
W. 96 L. 65 .596
Manager: Jim Frey
Best Player: Ryne Sandberg
Finished first in National League East
Lost to San Diego Padres 3 games to 2 in N.L. Championship Series 1989
W. 93 L. 69 .574
Manager: Don Zimmer
Best Player: Ryne Sandberg
Finished first in National League East
Lost to San Francisco Giants 4 games to 1 in N.L. Championship Series1998
W. 90 L. 73 .552
Manager: Jim Riggleman
Best Player: Sammy Sosa
Finished second in National League Central
Lost to Atlanta Braves 3 games to 0 in N.L. Division Series 2003
W. 88 L. 74 .543
Manager: Dusty Baker
Best Player: Mark Prior
Finished first in National League Central
Defeated Atlanta Braves 3 games to 2 in N.L. Division SeriesLost to Florida Marlins 4 games to 3 in N.L. Championship Series
2007
W. 88 L. 74 .543
Manager: Lou Piniella
Best Player: Mark Prior
Finished first in National League Central
Lost to Arizona Diamondbacks 3 games to 0 in N.L. Division Series
2008
W. 97 L. 64 .602
Manager: Lou Piniella
Best Player: Ryan Dempster
Finished first in National League Central
Lost to Los Angeles Dodgers 3 games to 0 in N.L. Division Series2015
W. 97 L. 65 .599
Manager: Joe Maddon
Best Player: Jake Arrieta
Finished third in National League Central
Defeated Pittsburgh Pirates in N.L. Wild Card GameDefeated St. Louis Cardinals 3 games to 1 in N.L. Division Series
Lost to New York Mets 4 games to 0 in N.L. Championship Series
2016
W. 103 L. 58 .640
Manager: Joe Maddon
Best Player: Kris Bryant
Finished first in National League Central
Defeated San Francisco Giants 3 games to 1 in N.L. Division Series
Defeated Los Angeles Dodgers 4 games to 2 in N.L. Championship Series
Defeated Cleveland Indians 4 games to 3 in World Series 2017
W. 92 L. 70 .568
Manager: Joe Maddon
Finished first in National League Central
Defeated Washington Nationals 3 games to 2 in N.L. Division Series
Lost to Los Angeles Dodgers 4 games to 1 in N.L. Championship Series
2018
W. 95 L. 68 .583
Manager: Joe Maddon
Best Player: Javier Baez
Finished second in National League Central
Lost to Colorado Rockies in N.L. Wild Card Game
2020
W. 34 L. 26 .567
Manager: David Ross
Best Player: Yu Darvish
Finished first in National League Central
Lost to Miami Marlins 2 games to 0 in N.L. Wild Card Series
("Best Player" based on Baseball Reference Wins Above Replacement.)
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