It is Day 16 of our 100-day countdown to kickoff. We are looking back at the 100 most iconic games in Dallas Cowboys history. The countdown will leads us right up to the opening game of 2026. Our look back doesn’t depend on just one criteria for our rankings. We take into consideration things like how big the game was for the organization, how memorable the game was, games that had unusual events take place, games that are a part of NFL lore, Cowboys firsts, and games where the Cowboys just plain
dominated. Variety is the spice of life and we have all different kind of Cowboys games to review. At the bottom, we’ll link each day of the countdown so you can go back and check out any you missed.
Strap in for Day 16 of our 100-day countdown to kickoff, when we revisit the afternoon the Cowboys’ 1990s dynasty first began to feel possible. Dallas went into Soldier Field with a young roster, a backup quarterback and no playoff victory since the 1982 season. But Jimmy Johnson’s team delivered the postseason breakthrough that opened the door to everything that followed.
Sunday, December 29, 1991 — 12:30 p.m. ET
Soldier Field, Chicago, Illinois
Final Score: Dallas Cowboys 17, Chicago Bears 13
The Cowboys, having finished 11-5, returned to the playoffs for the first time since 1985. However, Troy Aikman was still recovering from a knee injury, leaving Steve Beuerlein to start against an experienced Chicago team that had also gone 11-5. Despite the Bears producing more yardage throughout the afternoon, Dallas protected the football, created takeaways, and repeatedly stood firm near their own goal line.
Bill Bates helped create the opening points by forcing Jim Harbaugh to fumble on Chicago’s first possession. Defensive end Tony Hill recovered near midfield, and Ken Willis eventually converted a 27-yard field goal to give Dallas a 3-0 lead.
Special teams then presented another opportunity. Darrick Brownlow blocked a Bears’ punt, and Ken Norton Jr. recovered at the Chicago 10-yard line. Four plays later, Emmitt Smith scored from one yard out, extending the Cowboys’ advantage to 10-0 during the first quarter.
Chicago moved the ball effectively, but struggled to convert drives. During the second quarter, they reached the Dallas two-yard line, but Jack Del Rio and Tony Tolbert stopped consecutive rushing attempts, forcing a turnover on downs. Chicago later returned to the two-yard line but settled for Kevin Butler’s 19-yard field goal just before halftime, leaving Dallas ahead 10-3.
Butler added a 43-yard field goal during the third quarter to reduce the margin to four. Dallas answered with its most important offensive possession of the game, travelling 75 yards in 14 plays. Beuerlein kept the drive alive with two 22-yard completions to Michael Irvin before finding Jay Novacek for a three-yard touchdown on third-and-goal. The methodical response restored a 17-6 lead.
The Bears continued their relentless pressure in the fourth quarter. Another drive reached the Dallas seven, but Harbaugh’s fourth-down pass fell incomplete. However, Chicago eventually scored when Harbaugh connected with Tom Waddle for a six-yard touchdown, cutting the score to 17-13. This gave the Bears one final opportunity to secure the victory.
Mike Saxon’s 52-yard punt pinned Chicago at its own four-yard line with 1:50 remaining. Three plays later, Bates intercepted Harbaugh at the Bears’ 16, allowing Dallas to run out the clock. The veteran who connected the Landry era to Johnson’s rebuilding project had made the first and final defensive plays that shaped the victory.
This game belongs on the countdown because it was the moment Dallas’ young core gained postseason credibility. The Cowboys lost heavily at Detroit in the Divisional Round the following week, but the victory in Chicago proved the rebuilding process had reached a new stage.
Interesting Facts About the Game
The victory was Dallas’ first postseason win since defeating Green Bay in the 1982 NFC playoffs.
Countdown to kickoff
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