Ranking the top Chicago Cubs' postseason runs of the 21st century

The 21st century has seen the Cubs go on some of the best playoff runs in franchisea history

World Series - Chicago Cubs v Cleveland Indians - Game Seven
World Series - Chicago Cubs v Cleveland Indians - Game Seven | Ezra Shaw/GettyImages
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Over their 150-year history, the Chicago Cubs have had their fair share of struggles when it comes to the playoffs, but the 21st century has seen the organization play some of its finest October baseball.

Since 2000, the Cubs have secured a total of eight postseason berths and seen results range from a first-round elimination to winning a long-awaited World Series championship. These runs are ripe with iconic moments and historic meltdowns alike. Here is our ranking of the top Cubs' playoff runs of the last 25 years.

8. 2020: Eliminated in NL Wild Card Series

2020 is a hard year to quantify in baseball. Not only did the COVID-19 pandemic throw a wrench in the ability of MLB teams to safely play games, but the owners and players were also engaged in what turned into a bitter negotiation over baseball's collective bargaining agreement.

This made playing the 2020 season complicated to say the least, but we eventually got a 63-game season that everyone had to watch from home due to social distancing. The Cubs still had their core of players intact from the World Series run, with others like Yu Darvish, Ian Happ and Jeremy Jeffress helping lead the way.

This was also David Ross' first season as the team's manager after Joe Maddon was relieved of his duties. It was a pretty strange year all around but the team made the playoffs with a 34-26 regular season record. In the first year of the expanded playoffs, the Cubs faced the Miami Marlins in the National League Wild Card Series. The North Siders scored just one run over the two games and were swept out of their only postseason appearance of the 2020s to-date.

Given that the team started a major rebuild the following season and hasn't played October baseball since, the 2020 postseason is hard to look back on fondly. The only players remaining in the organization from that team are Nico Hoerner, Ian Happ and Brad Wieck. Tyson Miller and Colin Rea also briefly pitched for the Cubs in 2020 and saw stints with other teams before recently returning.

7. 2007: Eliminated in NLDS

In a way, 2007 was a time of rebirth for the Cubs. Their division rival St. Louis Cardinals were coming off a World Series victory in 2006 while the Cubs had finished last in the division. The Cubs were busy in the offseason, replacing manager Dusty Baker with Lou Pinella and acquiring several notable new players. Second baseman Mark DeRosa, starting pitchers Ted Lilly and Jason Marquis and outfielder Alfonso Soriano were signed in free agency, the latter of whom received the largest contract in team history until that point ($136 million).


These additions yielded fruitful results, and the Cubs went from last to first in the NL Central with 85 wins in 2007. But the postseason blues continued on the North Side as the Cubs were swept out of the division series by the Arizona Diamondbacks. Game 1 was the team's best chance to post a win, but the offense was unable to support six innings of one-run ball from ace Carlos Zambrano. But the team had a solid foundation to build on.

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