On January 28, 1996, Jerry Jones hoisted the Dallas Cowboys’ fifth Vince Lombardi Trophy. Little did anyone know back then that would be the last time the Cowboys would sniff a Super Bowl for the next three decades. 

Dallas has yet to make it back to an NFC title game since then, let alone a Super Bowl. The Cowboys’ playoff failures continued on Sunday as Dallas fell at home to the seventh-seeded Packers, the same franchise that handed Landry’s Cowboys two crushing playoff losses in the late ’60s. 

Jones’ franchise is now 5-13 in the postseason since defeating Pittsburgh in Super Bowl XXX. Of those 13 losses, several stick out more than the others. Here’s a look at the Cowboys’ five worst playoff losses over the past 28 years. The first game on our list shouldn’t be a surprise. 

1. 2023 NFC wild card 

Yep, Sunday night’s loss is the Cowboys’ worst playoff defeat over the last 28 years. Why? Because the Cowboys were the NFC’s No. 2 seed playing a Packers team that barely made the playoffs. And they were absolutely crushed in the first half.

Adding to the magnitude of this loss is the Cowboys having the NFL’s top-ranked offense and fifth-ranked scoring defense. Specifically, it surely hurt Jones to see Dak Prescott get outplayed by Jordan Love, a first-year starter who played Dallas’ defense like a fiddle. 

While a Super Bowl was ultimately the goal, it’s safe to say Cowboys fans would have been content with a hard-fought loss to the top-seeded 49ers, falling one game shy of the big game. Instead, Cowboys fans are once again dealing with an unsatisfying ending to a promising season. Rest assured that Jones won’t take his team’s most recent setback sitting down. 

2. 2007 divisional round 

On paper, the Cowboys’ best team since the ’90s was the 2007 squad that tied the franchise record for regular season wins (13). That team was led by future Hall of Famers Demarcus Ware, Terrell Owens, Jason Witten and Pro Bowl quarterback Tony Romo. 

Instead of a Super Bowl run, the ’07 Cowboys were shocked at home against the rival New York Giants in the divisional round. Giants quarterback Eli Manning threw two touchdowns to Amari Cooper, while his defense held the Cowboys’ high-scoring offense to just 17 points. 

New York sewed up its upset win with an interception in the end zone with 16 seconds left. The Giants parlayed that win into an improbable Super Bowl victory over the previously undefeated Patriots. 

3. 2014 NFC divisional round 

While no one knew it at this time, the 2014 season was the Cowboys’ last legitimate run with Romo under center. The Cowboys went 12-4 during the regular season before winning a thriller against the Lions in the wild-card round. 

Dallas was on the verge of upsetting the Packers in Lambeau Field the following week in the divisional round. But the Cowboys were on the wrong side of one of the most controversial calls in NFL history when the officials determined that Dez Bryant did not secure Romo’s fourth down throw late in the game that would have given the Cowboys the ball just short of the goal line. 

The Cowboys never got the ball back after Aaron Rodgers completed third-down completions to Davante Adams and Randall Cobb. 

4. 2016 NFC divisional round 

Similar to ’07, the ’16 Cowboys had a team of destiny feel. They enjoyed a magical season that was led by rookie phenoms Prescott and Ezekiel Elliott. The rookie duo led the Cowboys to a franchise-tying 13 regular season wins. 

Prescott was on the verge of leading the Cowboys to an epic comeback win against the Packers in the divisional round. Down 28-13, Prescott threw two touchdown passes in the fourth quarter and helped set up the game-tying field goal with 35 seconds left. 

With overcome looming, Rodgers instead stole Prescott’s thunder by making an absurd, 36-yard completion to Jared Cook that set up Mason Crosby’s game-winning, 51-yard field goal as time expired. 

5. 2006 NFC wild card round 

• Seahawks 21, Cowboys 20 

Dallas’ 2021 wild card loss to Green Bay was considered here, but the ’06 playoff loss was ultimately chosen for several reasons. For one, the Cowboys lost a game that would have snapped the franchise’s 11-year drought without a playoff win. The fact that the game was lost on a routine special teams play didn’t hurt, either. 

The Cowboys were a chip shot field goal away for taking a two-point lead over Seattle with 1:19 left. But Romo (the holder) fumbled the snap and was tackled from behind after he tried in vein to reach the end zone with his legs.