Bears - All Time Most Heartbreaking Losses

These are the losses that don’t just hurt on the scoreboard—they hurt the soul of the franchise.

The Heartbreak: The emotional whiplash.

The Stakes: NFC Divisional Round vs. the Rams at a snowy Soldier Field.
The Moment: Trailing 17-10 with 18 seconds left, the season looked over. facing a 4th-and-4, Caleb Williams backpedaled 20 yards to avoid a sack and heaved a desperate prayer off his back foot. The ball traveled over 50 yards in the air and found Cole Kmet in the back of the end zone to tie the game. It was instantly hailed as one of the greatest plays in franchise history.
The Pain: The high lasted less than ten minutes. On the opening drive of Overtime, a miscommunication between Williams and DJ Moore led to an interception by Kam Curl. The Rams drove down, and Harrison Mevis kicked the 42-yard game-winner to silence the frozen crowd.
Why it hurts: It felt like destiny. The "Miracle Heave" felt like the play that would finally exercise the demons of the Double Doink and the '10 NFC Championship. To lose on a turnover immediately after such a legendary play makes it sting in a completely unique way.

The Heartbreak: The "It Can’t End Like This" Loss.

The Stakes: NFC Wild Card game vs. the Eagles at Soldier Field.
The Moment: Trailing 16-15 with seconds left, Cody Parkey lined up for a 43-yard game-winning field goal.
The Pain: The kick looked good. Then it hit the left upright (Doink). Then it hit the crossbar (Doink). Then it fell harmlessly into the end zone. The sound of the ball hitting the metal twice is etched into Chicago sports history. It instantly killed the best Bears season in a decade.

The Heartbreak: The Rivalry Nightmare.

The Stakes: A trip to the Super Bowl on the line. At home. Against the Green Bay Packers.
The Moment: It wasn’t just one play; it was a slow bleed. Jay Cutler left with a knee injury (sparking a national media firestorm questioning his toughness). Third-string QB Caleb Hanie nearly led a miracle comeback, but his pass to B.J. Raji was intercepted for a touchdown (the "Big Guy" dance).
The Pain: Watching your arch-rivals celebrate winning the George Halas Trophy on your field, then going on to win the Super Bowl. It remains the closest the Bears have been to a title since 2006.

The Heartbreak: The Highest High to the Lowest Low.

The Stakes: The Super Bowl vs. Peyton Manning’s Colts.
The Moment: Devin Hester returned the opening kickoff 92 yards for a touchdown. At that exact second, every Bears fan believed they were destined to win.
The Pain: That was the peak. The rest of the game was a rainy, sloppy slow death. Rex Grossman turned the ball over, the defense couldn’t get off the field on 3rd down, and the Colts slowly grinded the Bears into submission 29-17. The tease of the opening kickoff made the result infinitely worse.

The Heartbreak: The Dagger.

The Stakes: Week 17 vs. the Packers. Winner takes the NFC North; loser goes home.
The Moment: With under a minute left, the Packers faced a 4th and 8 from the 48-yard line. The Bears brought pressure. Aaron Rodgers escaped to his left and floated a pass to a wide-open Randall Cobb, who walked into the end zone.
The Pain: The Bears had the division in their hands. A single defensive stop would have ended the Packers' season. Instead, Rodgers did what he always did, and the Bears missed the playoffs.

The Heartbreak: The Dynasty Killer.

The Stakes: Defending the 1985 Super Bowl title.
The Moment: The Bears went 14-2 and looked ready to repeat. But QB Jim McMahon was injured by a dirty hit earlier in the season (by Charles Martin). By the playoffs, the Bears were starting Doug Flutie. They lost to the Washington Redskins 27-13.
The Pain: This is the loss that ensured the '85 Bears were a "one-hit wonder" rather than a multi-year dynasty. The talent on that roster should have won 2 or 3 rings.

The Heartbreak: Perfection Denied.

The Stakes: The NFL Championship game.
The Moment: The Bears were 11-0, having outscored opponents 376–84. They were, statistically, perhaps the greatest team ever. They played the Redskins in the title game and lost 14-6.
The Pain: Losing a perfect season in the final game is a unique kind of torture that only the 2007 Patriots can truly understand.

Honorable Mention (The Modern Meltdown):

Week 1, 2018 vs. Packers: The Bears led 20-0. Khalil Mack was dominating. Aaron Rodgers left on a cart. Then Rodgers returned on one leg, threw three touchdowns, and the Packers won 24-23. It set the tone for the "Rodgers owns Chicago" narrative for his final years in Green Bay.