Chicago Cubs All-Time Lists

Ranking every Chicago Cubs team since 2000

(Photo by Jonathan Daniel/Getty Images)
(Photo by Jonathan Daniel/Getty Images) /
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Chicago Cubs: Even so-so clubs were better than most from previous decades

14) 2014

Record 73-89

The first half of the season was awful, but the second half saw better baseball and a look toward the future. Rizzo made his first All-Star game, Baez and Jorge Soler came up from the minors and Jake Arrieta began his dominant run as he pitched to a 2.53 ERA, 2.26 FIP and 0.99 WHIP in 25 starts.

13) 2005

Record 79-83

Derrek Lee’s MVP-caliber season was all Cubs fans really had. Him hitting 46 home runs with a .335/.418/.662 slash and 50 doubles was awesome. Everything else was just “blah”. Not terrible but not great.

12) 2009

Record 83-78

After back-to-back postseason-bound seasons in ’07 and ’08, the 2009 season was the very definition of mediocre. Expectations were very high, but they finished 7 1/2 games behind the Cardinals. The pitching staff regressed and the offense was not nearly as productive as the year before. It also did not help that Aramis Ramirez missed significant time due to a shoulder injury.

11) 2019

Record 84-78

Joe Maddon’s final season in Chicago was the only campaign in which the Cubs did not make the postseason during his tenure. Despite quality performances from the core players, the bullpen blew an insane amount of games and the defense was uncharacteristically bad. They looked out of focus and not even Nick Castellanos was enough to propel them back to October.

10) 2001

Record 88-74

Don Baylor’s squad surprised many with a competitive season. They did not make the postseason but they were in the thick of it right until the end. It was only the third season which the Cubs finished with over 85 wins since 1985. Sammy Sosa hit 64 home runs and starter Jon Lieber made the NL All Star team.

9) 2004

Record 89-73

Arguably the most disappointing ending to a regular season since 1969. The team was all-in on going to the World Series with a rotation of Mark Prior, Kerry Wood, Greg Maddux, Carlos Zambrano and Matt Clement. It ended with a collapse in the final week of the season which saw Sosa walk out on the final day and Steve Stone resigning from the TV broadcast booth after tension between him and organization piled up. It was ugly and frustrating despite winning 89 games.

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