Chicago sports history: 10 worst teams ever, including 2012 Chicago Cubs

Chicago Cubs
Credit: David Banks-USA TODAY Sports

David Banks-USA TODAY Sports

The city of Chicago has had its fair share of amazing championship seasons over the last 40 years. Everything from the Chicago Bears in 1985 and the Super Bowl Shuffle to the Chicago Cubs ending their 108 year World Series drought in 2016, to the Chicago Blackhawks dynasty run during the 2010’s, winning three Stanley Cups in six years.

Unfortunately, there have been a lot of bad seasons in between, especially of recent memory. The 2024 Chicago White Sox are on pace to be the worst team in baseball history, currently with a record of 21-58 and they are on pace to only win 40 out of 162 games but with the rest of their season to be determined, they are an honorable mention of worst seasons by a Chicago sports team for now.

With that in mind, this list will cover the 10 worst seasons of all time by Chicago sports teams. Apologies in advance to the fan bases of the Bears, Bulls, Blackhawks, White Sox and Cubs for triggering some bad memories.

Related: Worst MLB teams ever: 2024 Chicago White Sox chasing history, worst MLB teams of all time

10. 1932 Chicago White Sox

Credit: Brett Davis-USA TODAY Sports

Chicago White Sox pitching was a disaster

Credit: Brett Davis-USA TODAY Sports

9. 2018-19 Chicago Bulls

Credit: Quinn Harris-USA TODAY Sports

Coaching was fatal flaw for 2018-19 Chicago Bulls

Credit: David Banks-USA TODAY Sports

8. 2023-24 Chicago Blackhawks

Credit: Gary A. Vasquez-USA TODAY Sports

7. 2012 Chicago Cubs

Credit: Charles LeClaire-USA TODAY Sports

6. 1962 Chicago Cubs

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1962 Chicago Cubs offense was non-existent

Credit: Dennis Wierzbicki-USA TODAY Sports

5. 2016 Chicago Bears

Credit: Robert Deutsch-USA TODAY Sports

Losing hurt the 2016 Chicago Bears

Credit: Raj Mehta-USA TODAY Sports

4. 2003-04 Chicago Blackhawks

Credit: Jerome Miron-USA TODAY Sports

3. 2022 Chicago Bears

Credit: Wm. Glasheen/USA TODAY NETWORK-Wisconsin / USA TODAY NETWORK

2. 2000-01 Chicago Bulls

Credit: Jasen Vinlove-USA TODAY Sports

1. 1969 Chicago Bears

Credit: Mike Dinovo-USA TODAY Sports
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