Since 2000, the Cowboys have made the playoff nine times. But those years have been marked with playoff disappointment, with them never making an NFC championship in any of those nine playoff years. The Cowboys have won only three games in those nine playoff years, with the last coming in 2018. Although they might not have a lot of wins in those in the playoffs, the Cowboys have plenty of memorable playoff failures. Now, let’s go over the three worst playoff moments for the Cowboys.
3. “Referees’ Fault” – Cowboys vs. 49ers 2022
The 2021-2022 Cowboy season was a record-breaking year for the Cowboys. The Cowboys are 12-5, with the best offense in the league and the 7th best defense. Dak Prescott enjoyed 4,449 yards and a franchise-setting 37 touchdowns. On the defense side of the ball, they have an upcoming rookie linebacker, Micah Parsons. They had one of the best defensive players in the league. They also have Trevon Diggs, who led the league in interceptions with 11. After Week 18, the Cowboys earned 3rd place.
Their opponent would be the 49ers, a long-time rival of the Dallas Cowboys. The game would start badly for the Cowboys. They were down by 13 points in the second quarter, and by halftime, the score was 16-7. But down 13 points in the fourth quarter, the Cowboys would start to mount a comeback, and with 14 seconds left on the opponent’s 40-yard line, Dak would rush to the 23-yard line, but they would run out of time and would lose. After the game, Dak would initially blame the referees for the loss, but after review, it was determined that Dak would be at fault for not giving the ball to the ref.
(Final moments of the 2022 Wild Card game – CBS sports)
 2. Botch Snap – Cowboys vs. Seahawk’s 2006
2007 saw the rise of Tony Romo, who that season would take the place of Drew Bledsoe as the starting QB. Romo would lead the Cowboys to a 9-7 record and the 4th best offense in the NFL. Romo would pass for 2,903 yards and 19 touchdowns. His top target was Terrell Owens, with 1,180 receiving yards. He would also have running back Julius Jones, who rushed for 1,084 yards. Romo would clinch the 5th seed for the Cowboys, and their opponent would be the Seattle Seahawks.
The game was tightly contested throughout, but Seattle would take the lead by one point. But with one minute left in the game and the ball on the 2-yard line. All the Cowboys had to do was kick a field goal to take the lead. Their kicker of the time was Martin Gramática, whose nickname was “Automatica,” and one of the best place kickers at the time. But when they snap, the holder Tony Romo, would botch the snap and be forced to run to the end zone. He was two yards away from scoring a touchdown before he was tackled. The Cowboys lost the game and left an image of Tony Romo as a choker.
(2006 playoff Wild Card game – NBC)
1. #ItWasACatch – Cowboys vs. Green Bay 2014
2014 was indeed the year for the Dallas Cowboys. They posted a 12-4 record, having a three-way tie between the Green Bay Packers and Seattle Seahawks (Cowboys were 3rd seed). They had the 5th best offense, with the best running back, DeMarco Murray rushing for 1,845 yards. Tony Romo passed for 3,705 yards, with his number #1 receiver Dez Bryan having 1,320 yards, 8th most in the league. In the playoff, they barely scraped by a win against Matthew Stafford of the Detroit Lions (24-20). Then in the divisional round of the playoff, the Cowboys would face the Green Bay Packers at Lambeau Field.
The game would be a close contest throughout the game. DeMarco Murray would torch the Packer’s defense, putting up 123 yards, and their defense would get one turnover in the game. But with 4 minutes and 50 seconds left in the game, the Cowboys were driving down the field by 5 points. It was 4th down with 2 yards. Tony Romo would slug a long pass down to Dez Bryant, who would make a fantastic catch to put them at the 1-yard line. But the problem was that after reviewing the play, the referee reversed the call, making it incomplete. The Cowboys lost the game 21-26. If they won, the Cowboys could have made the Super Bowl that year, with them already beating the Super Bowl Champion Seattle Seahawks in the regular season. The last insult to injury was that the NFL would later say it was a catch.
(Dez Bryant’s reversed catch during the 2014 Divisional round of the playoffs – Fox NFL)