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Home»Other»The Chicago Bears’ Playoff Woes: A History of Heartbreak
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The Chicago Bears’ Playoff Woes: A History of Heartbreak

Zack PearsonBy Zack PearsonNovember 29, 20235 Mins Read
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The 2023 NFL season has reached its business end and the usual suspects are rising to the fore and announcing themselves as contenders. In the AFC, the Kansas City Chiefs appear to be head and shoulders above the rest of the competition. The reigning champions have managed to put a shocking opening-day defeat to the Detroit Lions behind them as they have built up an impressive 8-3 record. They are level in their conference with the Miami Dolphins while Lamar Jackson and his Baltimore Ravens are currently en route to top-seed status with one more victory. 

Over in the NFC, the powerhouse Philadelphia Eagles and San Francisco 49ers remain the teams to beat. The former have amassed a 10-1 record and the Super Bowl betting odds make them the +400 to put February’s heartbreak behind them and lift the Lombardi this term. But propping up the NFC North, just as they did last term, are the Chicago Bears. 

The Windy City side have had to endure yet another dismal campaign and are currently 3-8. To put just how poor that record is into perspective, only the Arizona Cardinals and the New England Patriots have a worse record in the entire league. This year has been a continuation of last season where the Bears managed to secure just three wins against 14 losses all season. So with their playoff records already extinguished, we decided now would be the best time to look back at the Bears’ most recent trips to the postseason. 

Wildcard Round Defeat to the Saints 

The most recent addition to the playoff follies came in the 2020 season. The Bears were limping into the postseason as the last wild-card team with a modest 8-8 record and as such, were paired against the formidable New Orleans Saints. To no one’s surprise, Chi-Town was defeated comfortably with a final score of 21-9. While the defence put up a commendable effort, the Bears’ offence sputtered throughout the game. The Saints’ defence kept the Bears’ running game in check, effectively neutralizing the offensive weapons they possessed. 

Wildcard Round Defeat to the Eagles 

In the 2018 season, the Bears entered the playoffs with a sense of optimism after topping the NFC North with a 12-4 record. They were facing the Philadelphia Eagles, but there was a feeling that coach of the Year Matt Nagy and his side had the tools to overcome them. Unfortunately, the game was fraught with missed opportunities, and ultimately, the Bears fell short, heartbreakingly losing by just one point, 16-15. The infamous Cody Parkey double-doink has been etched into the memory of every Bears fan, and other crucial dropped passes also contributed to the team’s downfall.

Packers Punch Their Ticket to the Super Bowl 

The 2010 season saw the Bears march to the Conference Championship, where they squared off against their rivals, the Green Bay Packers. It was a matchup of epic proportions, with the winner heading to the Super Bowl. Unfortunately, the Bears ended up losing 21-14 in one of the most bitterly disappointing games in franchise history. Cutler got hurt. Hanie was thrown in there. It was rough. 

The Packers went on to win the Super Bowl, so it wasn’t like they lost to some schmucks, of course. And Aaron Rodgers proved to the world just how good he is, winning MVP honours in both the regular season and the Big Game itself. For the Bears, it was the end of an era. They have reached the postseason just twice in the decade-plus since and they are without a postseason victory, since the win against the Seattle Seahawks that saw them secure the date with the Packers in the first place. 

Peyton Manning and the Colts Too Strong at Super Bowl XLI 

Now, let’s talk about the 2006 season, which was one of the most exciting years in recent Bears history. Led by an outstanding defence and a young quarterback named Rex Grossman, the Bears made it all the way to the Super Bowl. Unfortunately, they ran into Peyton Manning and the Indianapolis Colts, who won the game 29-17. Despite being underdogs heading into the game, there was optimism that the team could pull off a win. Unfortunately, this wasn’t to be, and it was hard not to feel crushed, especially considering that this was the Bears’ first – and so far last – trip to the Big Game. 

More Wildcard Agony at the Hanbds of the Panthers 

Last but not least, let’s look back at the 2005 season when the Bears made the playoffs for the first time since the 2001 season. They faced off against the Carolina Panthers in the wildcard round, but things didn’t go their way, and they lost 29-21, despite taking a 14-3 lead early in the game. This game was one that got away. A costly penalty on one end, and a missed opportunity on the other end, making for a frustrating fan experience overall.

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