Will Caleb Williams be next to leave a mark in Bears-Cowboys series?

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Jerry Jones' Cowboys come to Soldier Field for the first time since 2019 on Sunday as 1 1/2-point favorites, renewing an interesting series full of landmark type games even if the teams don't meet that often.
It's two teams once tied by the role Mike Ditka played for both in winning a Super Bowl as a player, assistant coach and head coach. Ditka and former Raiders coach Tom Flores are the only people ever to do this.
It's the 29th overall matchup between these teams Sunday and first since 2022, with Dallas ahead 16-12 including two playoff wins.
Ditka went 0-2 to start his career. Hurricane Ben is still in the forecast. pic.twitter.com/g6DHFnsFct
— Bears History (@ChiBearsHistory) September 16, 2025
Here are the most memorable 10 games in this series ranked.
10. 1962—Bears 34, Cowboys 33
A year before their NFL championship win over the Giants at Wrigley Field, the Bears went to the Cotton Bowl in November against the third-year team and needed to rally in the fourth quarter as Johnny Morris caught a 45-yard TD pass from Bill Wade and Roger LeClerc kicked the game-winning 15-yard field goal.
Bears J0HNNY M0RRIS. I was even a HS intern for him when he did local TV sports in Chicago. And to this day Morris is STILL the Bears all-time leading receiver. 5,059 yards. He retired 1967. He turns 90... next Friday! pic.twitter.com/fDAWly437Z
— Parker andTheMan (@parkerandtheman) September 21, 2025
9. 2022—Cowboys 49, Bears 29
The last game between the two. Justin Fields was ascending as a runner. They had a three-pronged running attack but this wasn't going to be enough to beat Micah Parsons at Dallas. Fields rallied the Bears from a 28-7 deficit with a 17-yard TD pass to N'Keal Harry and Khalil Herbert scored on a 12-yard run. Trailing 28-23, the floor collapsed as Tony Pollard scored on a 7-yard run and Parsons returned a fumble 36 yards to turn it into an easy Dallas win.
Micah Parsons recovers a fumble for his first NFL touchdown!pic.twitter.com/RHmq74zMZa
— America’s Team (@RoadToSix) June 20, 2023
8. 2012—Bears 34, Cowboys 18
One of Jay Cutler's great Bears games and Lovie Smith's as well. In a Week 4 game on Monday Night Football, Cutler threw for 275 yards on 18 of 24 and TDs to Devin Hester and Brandon Marshall. The Bears defense picked off Romo five times and made his 307 yards passing a moot point. Charles "Peanut" Tillman had an interception, as did Lance Briggs and the original D.J. Moore. Major Wright picked off two passes.
Bears kickoff ETA: 55 days
— Windy City Pick 6 (@WindyCityPick6) July 17, 2023
Lance Briggs picks off Tony Romo and takes it 74 yards for the score as the Bears dismantle Dallas 34-18.#DaBears
pic.twitter.com/EVXR4nncbf
7. 2010—Bears 27, Cowboys 20
A key momentum-building win in Week 2 for the Bears as they drove to the NFC championship game. Matt Forte caught a 3-yard TD pass from Jay Cutler with 5:16 left for a 27-17 Bears lead and they hung on to go 2-0 and drop Wade Phillips' team to 0-2. Cutler completed 22 of 29 for 277 yards and three TDs and the defense picked off Romo twice.
6. 1996—Bears 22, Cowboys 6
The Bears beat the defending world champions of Barry Switzer at Soldier Field to start the season on Monday Night Football. Because of injuries and holdouts, the Cowboys were without Michael Irvin and several others but the Bears held Emmitt Smith to 70 yards and won despite 87 yards receiving on nine catches from Deion Sanders. Erik Kramer completed 12 of 27 for 133 yards, Raymont Harris scored on a 33-yard wide receiver pass from Curtis Conway, Carlos Huerta kicked three field goals and Bryan Cox recovered a Cowboys fumble in the end zone.
This is the poster I had on my wall in Dallas back in 1970.
— Texas Wineaux (@Friscokid49) October 6, 2023
Keep in mind; I was a HUGE Dallas Cowboys Fan. Him and the Manster Randy White were my heroes!
Dick Butkus was a BEAST on the field! pic.twitter.com/EaZrGTSokb
5. 1992—Cowboys 27, Bears 14
The symmetry was obvious. Mike Ditka came to the Bears as coach from Dallas and his Bears coaching career ended there in a loss to the Cowboys. He was fired shortly thereafter. Will Furrer started at QB for the Bears in this loss to a Cowboys team headed to its second straight Super Bowl win under Jimmy Johnson. Furrer, a lefty, threw for 89 yards on 9 of 23 and Neal Anderson was held to 17 yards rushing.
✭ September 10th 1989: Brent Musberger, Irv Cross and Dick Butkus show an exposé of the New ERA Cowboys under Jimmy Johnson and Jerry Jones on The NFL Today. pic.twitter.com/G81bXvWKJV
— 90’s Dallas Cowboys (@90s_cowboys) September 11, 2022
4. 1971—Bears 23, Cowboys 19
At Soldier Field, Dick Butkus and the Bears defense produced seven takeaways and ruled the day, and Bobby Douglass supplied just enough offense to defeat a Cowboys team that went on to win the Super Bowl. In fact, the Cowboys never lost another game that season after this mid-season defeat, their third loss of the year. Doug Buffone, Charlie Ford, Garry Lyle and Ron Smith had interceptions as the Bears picked off Craig Morton three times and Roger Staubach once. Douglass ran in from 9 yards and threw a 28-yard TD pass to Dick Gordon as the Bears built a 23-12 lead in the fourth quarter. The Bears were outgained 481 yards to 194 but still won handily.
3. 1991—Cowboys 17, Bears 13*
The rise of Jimmy Johnson's team was confirmed with this wild-card round playoff defeat of Mike Ditka's team at Soldier Field, the last playoff game Ditka coached. The Bears trailed 10-6 in the third quarter after two Kevin Butler field goals but Jay Novacek caught a 3-yard TD pass from Steve Beuerlein to push it out of the Bears' reach. Tom Waddle caught a 6-yard TD pass from Jim Harbaugh in the fourth quarter but it wasn't enough. Waddle made nine catches for 104 yards and kept picking himself up off the turf repeatedly after what looked like bad injuries on big hits.
Cowboys officially hired former Bears HC Matt Ebeflus as their defensive coordinator. pic.twitter.com/hoK8g9PsvP
— Adam Schefter (@AdamSchefter) January 28, 2025
2. 1977—Cowboys 37, Bears 7*
After years of watching others get into the postseason, the Bears finally made it with a miracle run of six straight wins after they were 3-5 and a last-second overtime win in the snow and ice over the Giants in New Jersy. But once in the playoffs the Bears were badly outclassed by the Cowboys, who went on to beat Denver in the Super Bowl. The Cowboys led 37-0 and the only Bears score was Steve Schubert's 34-yard TD from Bob Avellini. The "Doomsday defense" held Walter Payton to 60 yards on 19 carries while Dallas' Tony Dorsett had 85 rushing yards and Robert Newhouse 80.
September 16, 1979
— hoopsjunky (@hoopsjunky54491) September 16, 2025
Roger Staubach passed for 222 yards and 3 touchdowns in the Cowboys 24-20 win over the Chicago Bears. pic.twitter.com/QGXqM5mUES
1. 1985—Bears 44, Cowboys 0
Buddy Ryan's 46 defense announced its arrival at Dallas with authority, as Steve McMichael, Dan Hampton, Otis Wilson and Dave Duerson recorded sacks, Richard Dent made two sacks and a TD interception return, Mike Richardson scored a TD on an interception returns and Les Frazier and Ken Taylor also intercepted passes at Dallas. The defense knocked QB Danny White out of the game, then backup Gary Hogeboom and White had to come back in. Then Hogeboom came back and finished. Payton ran or 132 yards to lead the offense. The Bears locked up their division early with the win.
The Bears then rolled on to win Super Bowl XX 46-10 over New England.
*-Playoff game
November 17, 1985
— Kevin Gallagher (@KevG163) November 17, 2023
"44-0"
The #Bears run their record to 11-0 by handing the #Cowboys their worst loss in franchise history — 44-0 at Texas Stadium.
The win clinches the NFC Central crown — #Chicago's first division title in 22 years. It also is the first time that Mike Ditka… pic.twitter.com/Q0Au1umeBL
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Gene Chamberlain has covered the Chicago Bears full time as a beat writer since 1994 and prior to this on a part-time basis for 10 years. He covered the Bears as a beat writer for Suburban Chicago Newspapers, the Daily Southtown, Copley News Service and has been a contributor for the Daily Herald, the Associated Press, Bear Report, CBS Sports.com and The Sporting News. He also has worked a prep sports writer for Tribune Newspapers and Sun-Times newspapers.