The NFL is a “what have you done for me lately” league. Leashes are short for coaches and quarterbacks. People are often judged by their last game. And if a franchise isn’t making frequent postseason appearances, or at least a few deep postseason runs, broad changes are made. For the Bears, 1985 is often used as a reference point. It’s the last time they won the Super Bowl, and it’s often regarded as one of the best teams in NFL history. Since then, the Bears have had a few stretches of sustained success, but on the whole it’s been more bad than good. Scroll on to see the full Bears playoff history since that one storied season.
1986 - LOST IN DIVISIONAL ROUND TO WASHINGTON, 27-13
This is probably the most shocking loss in Bears history, since most thought the Bears were on the way to building a dynasty. The defense was arguably more dominant, since they allowed only 187 points in the regular season, compared to 198 in ‘85. Walter Payton put together his 10th 1,000 rushing yard season. The Bears earned a bye in the playoffs with a 14-2 record, but they were upset at home in their first game. Washington outscored the Bears 20-0 in the second half to complete the shocker, and instead of 1986 being the next step in a Bears dynasty, it was the beginning of the end.
1987 - LOST IN DIVISIONAL ROUND TO WASHINGTON, 21-17
Walter Payton announced at the end of the 1986 season that 1987 would be his last, so the team wanted him to go out with a bang. Instead, the Bears took a step back in a strike-shortened season to finish with an 11-4 record, but that was still good enough to win the NFC Central and lock up a bye in the playoffs. Once again, the Bears took on Washington with a chance to avenge their stunning loss from the year prior. Things looked good, as the Bears got out to an early 14-0 lead, but Washington got the best of them again and went on to win Super Bowl 22.
1988 - LOST IN CHAMPIONSHIP GAME TO 49ERS, 28-3
The Bears earned home field advantage throughout the playoffs after a 12-4 season highlighted by a Defensive Player of the Year campaign by Mike Singletary. Thankfully the Bears didn’t have to play Washington in the Divisional Round, and got a win against the Eagles in what’s now known as The Fog Bowl. But in the NFC Championship game, Joe Montana (288 yards, three touchdowns, no interceptions) outplayed Jim McMahon (121 yards, no touchdowns, one interception), and the Bears were blown out at Soldier Field. It ended up being McMahon’s last hurrah with the Bears. He was traded to the Chargers in the offseason and the team moved forward with 1987 first-round pick Jim Harbaugh.
1990 - LOST IN DIVISIONAL ROUND TO GIANTS, 31-3
The Bears missed the playoffs in 1989 for the first time since 1986, but made a quick comeback. They weren’t the same dominant squad of the 80s, though and finished third in the NFC. Mike Tomczak and Neal Anderson were good enough to get by the Saints in the Wild Card round, in what ended up being Mike Ditka’s last playoff win with the Bears. Because in the Divisional Round the Bear got stomped by the eventual Super Bowl champion Giants.
1991 - LOST IN WILD CARD ROUND TO COWBOYS, 17-13
Jim Harbaugh missed the 1990 playoffs due to a shoulder injury, but he was good to go in 1991. It ended up being his only playoff game in a Bears uniform since they lost their first game to the up-and-coming Cowboys. Harbaugh was gone by the time the Bears returned to postseason play.
1994 - LOST IN DIVISIONAL ROUND TO 49ERS, 44-15
The Bears finished fourth in the NFC Central with a 9-7 record, in Dave Wannstedt’s second season as head coach. In a down NFC that was still good enough to make the playoffs as the six seed. Backup QB Steve Walsh led a surprising upset over the divisional rival Vikings in the Wild Card round with a big 35-18 win, but it all came crashing down with a beat down at the hands of Steve Young and the 49ers one week later.
2001 - LOST IN DIVISIONAL ROUND TO EAGLES, 33-19
Just like Wannstedt, Dick Jauron led the Bears to the playoffs in his second season. Just like Wannstedt, it would be his only playoff appearance with the Bears. The Bears surprisingly went 13-3 with improbable moments, like Mike Brown’s back-to-back walkoff pick-sixes against the 49ers and Browns. Running back Anthony Thomas won Rookie of the Year, the defense was great and things were looking up for the franchise. But the curse of hurt quarterbacks in the playoffs continued. Jim Miller got hurt in the second quarter, Shane Matthews was forced to come in, and the Bears lost in embarrassing fashion.
2005 - LOST IN DIVISIONAL ROUND TO PANTHERS, 29-21
The trend of Bears head coaches making the playoffs in their second season continued with Lovie Smith in 2005. This time, the Bears would have some sustained success however. The Bears earned a bye behind a strong defense that was led by Defensive Player of the Year Brian Urlacher. But once again, they lost their opening postseason game.
2006 - LOST IN SUPER BOWL TO COLTS, 29-17
The Bears came back in 2006 much better, and with a rookie phenom named Devin Hester. It felt like a season of destiny after a 7-0 start and two big wins in the Divisional Round and in the NFC Championship game. First, the Bears beat the Seahawks with a clutch 49-yard field goal from Robbie Gould in overtime. Then, the defense put the clamps on Drew Brees, Reggie Bush and the Saints for a dominant 39-14 win as snow fell in Soldier Field. For the first time since 1985, the Bears were headed to the Super Bowl. Hester started the game in ridiculous fashion with the first opening kickoff touchdown in Super Bowl history, but things went downhill from there. Rex Grossman threw two interceptions and lost a fumble. Cedric Benson lost one too. Meanwhile, the Bears’ typically stout run defense couldn’t stop Dominic Rhodes or Joseph Addai. The Bears haven’t been back to the Super Bowl since.
2010 - LOST IN NFC CHAMPIONSHIP TO PACKERS, 21-14
Stop me if you’ve heard this one before: The Bears lost their quarterback in the playoffs and the backup fell short of leading the team to victory. That’s what happened yet again when Jay Cutler injured his knee partway through the NFC Championship game. Caleb Hanie put up a valiant effort to knock off the Packers and send the Bears to the Super Bowl, but he threw an interception on the team’s last drive of the game to squash any hopes of a comeback.
2018 - LOST IN WILD CARD ROUND TO EAGLES, 16-15
Matt Nagy broke the trend and led the Bears to the playoffs in his first season as head coach. Once again the Bears felt like a team of destiny led by Vic Fangio’s electric defense. Of course those dreams were dashed in the opening round of the postseason. Everyone remembers the double doink, but many forget it was the vaunted defense that allowed the Eagles to score when the Bears took a 15-10 lead in the fourth quarter.
2020 - LOST IN WILD CARD ROUND TO SAINTS, 21-9
Following 2018’s success, the Bears had two disappointing 8-8 seasons in a row. But in 2020, that middling record was good enough to slide into the newly-created No. 7 seed. The Bears didn’t belong in the playoffs and it showed. They didn’t score a touchdown until the final play of the game, which made the final score look less embarrassing. There was a silver lining however: Mitchell Trubisky made history by winning Nickelodeon’s very first NVP award.
There you have it. Lots of promising seasons undone by injuries and early exits. Since the Bears won the Super Bowl they’ve gone 6-12 in the postseason and are still looking for their second Lombardi Trophy.