The Pittsburgh Steelers history vs the Chicago Bears is long and rather tortured for Pittsburgh, dating back to 1934, with the Steel City suffering a 7-22-1 record against Windy City.

The founders of both franchises, Art Rooney Sr. and George Halas are both members of the Pro Football Hall of Fame. While the lopsidedness of the Steelers history vs. the Bears might be due to Pittsburgh’s ineptness during the pre-Chuck Noll era, Pittsburgh’s record in Chicago remains a woeful 1-12.

This chronicle of Steelers history vs the Bears only goes back 35 years that have seen Pittsburgh square off against Chicago 9 times. Indeed, a see-saw dynamic characterizes recent Steelers-Bears history, as the Steelers seem to celebrate glorious victories or agonizing defeats, with very little in between.

Either scroll down or click on the links below to relive key moments in the Pittsburgh Steelers history vs. the Chicago Bears:

Antonio Brown catches a touchdown in front of Charles Tillman of the Bears. Photo Credit: Jason Bridge, USA Today

1986 – Ditka Takes the Wind over the Ball in OT

November 30, 1986 @ Solider Field
Chicago 13, Pittsburgh 10

The 4-8 Steelers gave the defending Super Bowl Champion Bears a run for their money, even though they did not score an offensive touchdown. But that was good enough to force overtime when…

Iron Mike elected to kickoff, trusting in the wind and his defense. The Bear’s defense vindicated their coach, forcing a punt and setting up Kevin Butler’s winning kick.

• Fun Fact: The Steelers only touchdown came in the third quarter on a fake field goal from Harry Newsome to tight end Preston Gothard.

1989 – Steelers Suffer Third Shut Out of Season

November 11, 1989 @ Three Rivers Stadium
Chicago 20, Pittsburgh 0

Aliquippa native Mike Dikta gave himself a hell of a home coming during the only game he coached at Three Rivers Stadium. His Bears netted 6 turnovers, wracked up 203 rushing yards, and held Pittsburgh to 54 rushing yards during their 20-0 shut out.

• Word to the Wise – Steel Curtain Rising gave this game an in depth look in our tribute to the 1989 Steelers. But this third shut out at the hands of the Bears knocked the ’89 Steelers to 4-6 and caused all but a few to write the 1989 Steelers off for good. Oh, how they were mistaken….

1992 – Cowher’s Achilles Heel or Mike Singletary’s Final Game in Chicago?

December 13, 1992 @ Solider Field
Chicago 30, Pittsburgh 6

Rookie head coach Bill Cowher’s 1992 Pittsburgh Steelers had taken the NFL by storm. They traveled to Chicago with a 10-3 record and a chance to clinch their first AFC Central Title since 1984. Cowher Power had rejuvenated the Steelers.

• The sky was the limit. Or was it?

The Cowher’s Steelers fell flat on their faces. And then the Bears stomped all over them, to the tune of 30-6. Barry Foster ran 12 times for 25 yards. The Bears sacked Bubby Brister 5 times and picked him off twice. Worst of all, Pittsburgh looked lethargic and unfocused.

NBC commentator Bill Parcells attributed the result to the emotional surge occasioned by Mike Singletary’s final game in Chicago, sharing something to the effect, “I was in the Bear’s locker room prior to the game, and this was a team clearly ready to play.”

• Cowher’s Admission: During Cowher’s early tenure, over confidence was his Steeler’s chronic Achilles heel. Cowher would perhaps dispute this general observation, but a number of years later he admitted that the 1992 game against the Bears was one of the few times the team had not been mentally prepared to play.

Greg Lloyd closes in on the Bears Rashaan Salaam in the Steelers 1995 win over the Bears. Photo Credit: Jonathan Daniel, Getty Images via the Bleacher Report

1995 – Steelers Streak to the Super Bowl, Vol. I – Super Bowl XXX

November 5th, 1995
Pittsburgh 37, Chicago 34

The 1995 Steelers started 3-4, and looked ugly doing it. After a particularly egregious loss to the Cincinnati Bengals, Bill Cowher declared it was now a “9 game season.” Having beaten the Jaguars in week 8, they traveled to Chicago to take on the 6-2 Bears.

• This was one of the most exciting games the Steelers have every played.

The lead changed 5 times and the score was tied 3 times as the Steelers and Bears fought back and forth in this titanic struggle.

Hope faded for the Steelers when Barry Minter returned an interception to put the Bears up 34 to 27 late in the fourth. But Neil O’Donnell rebounded, taking the Steelers the length of the field capping off the drive with a 11 yard strike to Ernie Mills to tie it up just inside the two minute warning.

Cowher seemed ready to gamble it all when he sent in the 2 point conversion unit, forcing the Bears to burn their final time out. The Steelers kicked the extra point instead, and Willie Williams picked off Eric Kramer in OT, to set up Norm Johnson’s game winning field goal.

• Cowher’s Quote: When asked if such a dramatic victory might have been a character building exercise for his recently struggling Steelers, Cowher’s response was concise and correct – “Games like this do not build character, they display it.”

That character carried the Pittsburgh Steelers to Super Bowl XXX

1998 – Steelers Start season 2-0, But…

September 13, 1998 @ Three Rivers Stadium
Pittsburgh 17, Bears 12

The 1997 Steelers had finished 11-5 and only two Kordell Stewart end zone interceptions away from the Super Bowl. But the 1998 Steelers were a differnt story. They’d beaten the Ravens 20-13 the week before, but had not looked good doing it.

The Steelers defeated the Bears 17-12 on the strength of Jerome Bettis 131 years rushing.

• Cause for concern: Kordell Stewart went 17-30-1-1. Not bad numbers, but he only threw for 137 yards and was only 4-4 rushing. Whether it was because Ray Sherman didn’t know what he was doing, or a lack confidence, but this was the beginning of a tentative and timid Stewart, as opposed to the swashbuckling Slash that Steelers fans had seen before.

2005 – Steelers Streak to the Super Bowl, Vol. II Super Bowl XL

December 11, 2005 @ Heinz Field
Pittsburgh 21, Chicago 9

The Bears were coming off an 8 game winning streak. Despite their 7-5 record, the 2005 Steelers were coming off a 3 game losing streak, and looking at the possibility of needing to run the table to make the playoffs. The Steelers were up to the task, as the Bus led the march that ended with One for the Thumb in Super Bowl XL.

Jerome Bettis shows Brian Urlacher who is boss. Photo Credit: Ezra Shaw, Getty Images via The Sun.

The Steelers totally dominated the Bears in the snow at Heinz Field. Jerome Bettis ripped off 101 yards as he plowed through Brian Urlacher and the Bears defense. Willie Parker was close behind him with 68 yards. Ben Roethlisberger hit seven different receivers, as the Steelers out gained the Bears by almost 100 yards, and dominated time of possession to the tune of 37:19 to 22:41

• Bettis Final 100 Yard Game: This was Bettis’ 50th 100 yard game with the Steelers, a team record. It was also to be the Bus’ final 100 yard effort, and he gained all but one of them in the second half. He also scored 2 TD’s for the 16th time in his career, which brought him to 4th on the Steelers all-time scoring list.

2009 – Super Bowl Champion Steelers Slip, Signal Things to Come…

September 20th, 2009 @ Solider Field
Chicago 17, Pittsburgh 14

The defending Super Bowl Champions had won their opener doing what they had done during the previous season – snatching victory from the jaws of defeat. But this trip to Solider Field showed that things would not be so easy for the 2009 Steelers.

The Steelers got on the board quickly with a clockwork like opening drive engineered by Ben Roethlisberger. But Roethlisberger threw an interception and he was off after that, overthrowing and underthrowing receivers and throwing balls that were either too low or two high. Ben Roethlisberger had help however,

• Santonio Holmes had several drops
• James Harrison got called for an inane illegal contact penalty for merely brushing up against Jay Cutler
• Jay Cutler made swiss cheese of a Troy Polamaluless Steelers secondary

Despite that, the Steelers hung in and appeared to be set to repeat history – pull out a win at the last moment.

Unfortunately Jeff Reed missed a long field goal, giving Chicago a victory. Unlike their ’08 brethren, this was to be the first of many last minute losses for the ’09 Steelers….

2013 – Bears Pass Rush Overwhelms Steelers en Route to 0-3 Start

Sometimes single tweet says it all. That’s the case with this Dale Lolley gem that still resonates long after the Steelers 2013 loss to Chicago:

Bears sending more than #Steelers can block. Apparently that's one

— Dale Lolley (@dlolley_pgh) September 23, 2013

• That might seem like a harsh exaggeration, but rest assured my fellow citizens of Steelers Nation, it is not.

The 2013 Steelers entered the game at 0-2, yet both of those games had some extenuating circumstances (such as losing 3 starters in their opener to the Tennessee Titans.) But this was the height of the Mike Adams experiment on offensive line and, truth be told, the jury was still very much out on Marcus Gilbert at that point.

Ben Roethlisberger barley had time to breath, let along throw that night, as the Steelers signal’s turnovers directly led to two Bear’s touchdowns. Chicago jumped to a 27-3 lead, until a Ben Roethlisberger to Antonio Brown hookup evened the score to 27-10 at the half.

• The Steelers opened the 2nd half by 13 unanswered points to bring it to 27-23 by the beginning of the 4th quarter.

Alas, a Jay Cutler scramble on 3rd and 10 gave Chicago new life, and set up a score. The Steelers tired to match, but a Roethlisberger fumble was returned to Pittsburgh’s six yard line and the Steelers started 2013 0-3.

2017 – Trap Game Trips Up Steelers Fueled by Breakdowns in All 3 Phases

September 24th, 2017 @ Solider Field
Chicago 23, Pittsburgh 17 in OT

This was the infamous “National Anthem” game when the Steelers opted not to take the field to avoid controversy only to have Alejandro Villanueva exit the tunnel to observe the ceremony. So much for trying to use team unity as a way of abstaining from political polemics.

• Things went downhill from there.

Jordan Howard (who?) looked like Gale Sayers and Walter Payton — combined — drilled the Steelers for 140 yards. His compatriot Tarik Cohen (who?) “only” ran for 78 yards, so I guess he must have just been Neal Anderson. The Steelers offense, featuring all four Killer Bees, struggled to establish the run and Antonio Brown bailed Ben Roethlisberger out throughout the afternoon.

• Worse yet, special teams gave up a blocked field goal AND suffered a muffed punt.

Take away:  This game exposed the run defense as the 2017 Steelers Achilles heel.

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