The Chicago Bears haven’t won a playoff game in nearly 15 years, and Saturday night’s Wild Card matchup against the Green Bay Packers at Soldier Field represents a chance to end that drought.
Chicago’s last postseason victory came on Jan. 16, 2011, when Jay Cutler and the Bears dismantled the Seattle Seahawks 35-24 in the Divisional Round. Let’s revisit that game and this team’s chances of duplicating their success.
How the Bears Won Their Last Playoff Game
The 2010 Bears entered the postseason as NFC North champions and the No. 2 seed — sound familiar? They earned a first-round bye and hosted a Seahawks team that had no business being there. Seattle won the NFC West at 7-9, the worst record by a division champion in NFL history at the time.
None of that mattered once Chicago got rolling. Greg Olsen hauled in a 58-yard touchdown on the game’s opening drive, and the Bears never looked back. Cutler finished with 274 passing yards, 43 rushing yards, and four total touchdowns — two through the air and two on the ground. Matt Forte grinded out 80 yards on 25 carries. Brian Urlacher anchored a defense that built a 28-0 lead before Seattle mounted a futile late rally.
It was Cutler’s first playoff game. It would be his only playoff win.
The following week brought heartbreak at Soldier Field. The Packers rolled into Chicago and left with a 21-14 NFC Championship victory that sent them to Super Bowl XLV. Cutler exited with a knee injury, third-stringer Caleb Hanie couldn’t spark a comeback, and B.J. Raji’s pick-six sealed it. Green Bay went on to beat Pittsburgh for the Lombardi Trophy.
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The Bears have made just two playoff appearances since — a Wild Card loss to the Eagles in January 2019 (Cody Parkey’s “Double Doink”) and a 21-9 defeat to the Saints in January 2021. Neither game was particularly competitive.
Can Caleb Williams End the Drought on Saturday?
Fifteen years is a long time. While the Miami Dolphins hold the longest active playoff-win drought in the NFL (25 years), the Bears have the longest active streak in the NFC. Chicago’s nine-championship history, including the 1985 Super Bowl, makes the drought feel even more pronounced.
Caleb Williams doesn’t seem bothered by the weight of it.
“I am built for these moments,” Williams told reporters Tuesday at Halas Hall. “I’ve been in a bunch of big games before. A bunch of big rivalry games. I can do whatever my team needs me to do, whether that’s stay in the pocket, whether that’s run, whether that’s scramble, hand the ball off 30 times, and be energetic about it, whatever it takes.”
Williams’ second season has been defined by late-game heroics. He’s engineered six game-winning drives — the most by any NFL team since the 1970 merger. In the final two minutes of the fourth quarter or overtime with a chance to tie or win, the Bears are 6-1 when Williams has the ball. His Week 16 performance against these same Packers cemented his reputation as a cold-blooded closer, as he threw a 46-yard overtime touchdown to DJ Moore after trailing by 10 with under two minutes remaining.
“He was built for these moments,” Johnson said. “He plays his best when we need him to.”
The concern is the starts, not the finishes. Slow starts have been an issue for Chicago. Playoff football punishes teams that dig early holes. The Packers won’t be the pushovers; Jordan Love gives Green Bay legitimate comeback ability of its own, and the NFC’s oldest rivalry has a way of producing chaos.
Saturday marks just the third playoff meeting between these franchises. They split the first two: a 1941 divisional game won by Chicago and that 2010 NFC Championship claimed by Green Bay. A win for Williams would make him the first Bears quarterback to beat the Packers twice in a single season (including the playoffs) since Jim Harbaugh in 1991.
Fifteen years is long enough. Chicago has the quarterback, the home-field advantage, and a team that’s proven it can find ways to win when it matters most. Whether Williams can deliver will determine if Bears fans finally have a new playoff memory to celebrate or another decade of waiting.
