Bears Playoff History | Vintage Chicago Tribune

by Ethan Brooks

CHICAGO, December 23, 2025 – The Chicago Bears have experienced the highs and lows of postseason play as 1932, culminating in two Super Bowl appearances but ultimately falling short of a championship title in the modern era. The team’s playoff history, spanning decades, reveals a narrative of both thrilling victories and heartbreaking defeats.

A Legacy of Playoff Battles

A look back at the Bears’ postseason journey, from their early dominance to their Super Bowl bids.

  • The Bears first participated in a playoff game in 1932, showcasing a long tradition of postseason competition.
  • The team secured a championship in 1933, predating the Super Bowl era.
  • Chicago reached the Super Bowl twice, in 1986 (Super Bowl XX) and 2007 (Super Bowl XLI), but lost both times.

The Bears’ initial foray into playoff contention began in 1932, marking the start of a storied postseason history.In 1933, the team achieved championship glory, defeating the Portsmouth Spartans in a championship game. This victory established the Bears as a dominant force in the early days of professional football.

did you know? – The bears’ 1933 championship was decided in a controversial game played in freezing temperatures, with the Bears winning 26-17.

Following World War II, the Bears continued to be a competitive force, reaching the championship game several times. The team’s success in the 1940s and 1950s solidified it’s reputation as one of the NFL’s premier franchises.

Navigating the Post-War Era

Following World War II, the Bears continued to be a competitive force, reaching the championship game several times. The team’s success in the 1940s and 1950s solidified its reputation as one of the NFL’s premier franchises.

What was the outcome of the Bears’ Super Bowl XX appearance? The Bears lost to the New England Patriots 46-10 in Super Bowl XX, despite a dominant regular season.

Pro tip – Studying the 1985 Bears defence reveals a blueprint for defensive success: relentless pressure and opportunistic turnovers.

The advent of the Super Bowl era brought new challenges and opportunities for the Bears. The team experienced periods of both success and struggle, but remained a consistent presence in the NFL landscape. The 1985 Bears, led by quarterback Jim McMahon and a ferocious defense, captured the imagination of the nation and advanced to Super Bowl XX.

Super bowl Dreams and Recent History

Despite a dominant regular season in 1985, the Bears fell short in Super Bowl XX, losing to the New England Patriots. The team’s second Super Bowl appearance came in 2007, where they faced the Indianapolis Colts in Super Bowl XLI. However, the Colts emerged victorious, dashing the Bears’ championship hopes once again.

In more recent years, the Bears have struggled to consistently reach the playoffs, facing challenges in quarterback play and overall team consistency. The franchise continues to seek a return to its former glory, aiming to once again compete for a Super Bowl

Reader question – What do you think is the biggest obstacle preventing the Bears from winning a Super Bowl? Share your thoughts!

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