The 10 Most Devastating Dallas Cowboys Losses Since 2000

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Each season, 31 NFL teams and fan bases are disappointed with how their season played out. It makes sense because there can only be one Super Bowl champion.

This leaves plenty of chances for fans to be crushed by big time losses throughout the year. But for some reason, it seems like the Cowboys are especially doomed to lose in dramatic fashion each and every time they make the playoffs.

Here are the 10 most painful regular season and postseason losses since the 2000 season:

10. Rams 30, Cowboys 22 – Divisional Round 2018 playoffs

Dallas exceeded expectations in 2018. Oddsmakers projected them to only get 8.5 wins, but a 10-6 record won them the NFC East and the first wild card spot in the postseason.

The Cowboys were red hot to finish the year, going 7-1 in the final eight games. They rode the momentum to beat the Seattle Seahawks in the Wild Card Round.

But the fun came to an end when Dallas traveled to Los Angeles to face the soon-to-be NFC champion Rams. Los Angeles imposed its will in the trenches, rushing for a total of 273 yards. The leaders in the clubhouse were C.J. Anderson with 123 yards and Todd Gurley with 115 yards.

9. Eagles 41, Cowboys 14 – Week 1 2000

Things were doomed from the opening kickoff for Dallas. Eagles kicker David Akers opened the game with an onside kick recovered by Philadelphia.

From there, it was all about Eagles running back Duce Staley. Philadelphia had 129 yards of offense in the first quarter, and Staley accounted for 109 of them.

When it was all said and done, Staley had 201 rushing yards, 61 receiving yards and one touchdown. As a team, Dallas gained only 167 yards of offense after Troy Aikman left with an early injury.

8. Texans 19, Cowboys 10 – Week 1 2002

No matter how much the odds may be stacked against a team, they can still win on any given Sunday. But when the Texans, who joined the NFL as an expansion team in 2002, beat the Cowboys, it was downright sad for Dallas fans. It was the first time since 1961 that an expansion team won its opening game.

David Carr led Houston, who was drafted first overall in 2002 out of Fresno State. Carr threw for 145 yards, two touchdowns and two interceptions in his debut.

7. Redskins 22, Cowboys 19 – Week 9 2006

With 33 seconds left and the score knotted at 19, Redskins kicker Nick Novak came out to attempt a 49-yard field goal, but he pushed it far right.

Then, with six seconds remaining, it was Cowboys kicker Mike Vanderjagt’s turn to try a 35-yarder. But it was blocked by Troy Vincent and scooped up by Sean Taylor, who returned the ball to Dallas territory.

Initially, time had run out, and the game was headed to overtime. But a Cowboys player was flagged for grabbing Taylor’s facemask during the return, so Washington got an untimed down to end regulation.

Out came Novak, but this time he nailed the 47-yard field goal and Washington stole the victory. This was the only time since 2000 that a field goal won the game immediately after the losing team had a field goal try blocked.

6. Eagles 44, Cowboys 6 – Week 17 2008

Heading into the season’s final week, the Cowboys and Eagles had nearly identical records, and the winner would claim the second wild card spot in the playoffs.

The Eagles came ready to play. By halftime, Philadelphia was up 27-3. But things only got worse in the second half, with Dallas losing by a total of 38 points. The Cowboys couldn’t even give the fans a touchdown to cheer for in the embarrassing loss to a bitter rival.

Some days you’re the hammer and some days you’re the nail. In this game, the Eagles were more like a sledgehammer. 

5. 49ers 23, Cowboys 17 – Wild Card Round 2021 playoffs

This loss is the freshest in the minds of the Cowboys faithful. Dallas ended the season on a high note, going 5-1 in the final six games. The offense was spectacular all year, averaging a league-best 31.2 points per game. So piecing together only 17 points made this loss even harder to watch.

But what would a Cowboys loss be without some dramatics to end the game?

Dallas trailed by six with 14 seconds remaining and no timeouts. It had the ball in 49ers territory. Dak Prescott opted to rush the ball up the middle to improve field position and then tried spiking it with seconds left to run one final play. The only problem was the referee bumped into Prescott on his way to down the ball, causing time to expire before getting the snap off.

4. Packers 34, Cowboys 31 – Divisional Round 2016 playoffs

Aaron Rodgers is a bad, bad man. He’s no stranger to late-game heroics, and it was on full display at the end of this game. But he also had a ton of help from his kicker Mason Crosby when they knocked Dallas out of the playoffs in 2016.

With 1:33 left in the game, Crosby knocked in a 56-yard field goal to give the Packers a 31-28 lead. But the Cowboys marched down the field and set up Dan Bailey to hit a 52-yard field goal, tying the game up with only 35 seconds to go.

While most viewers were mentally preparing for overtime, Rodgers’ was still focused on ending the game in regulation. Rogers’ dropped a 35-yard dime to Jared Cook when it seemed like he was going to throw the ball away. This set up a game-winning field goal try with 3 seconds left. Then, Crosby came back out and split the uprights from 51-yards out as time expired.

To make matters worse, Dallas was the first seed in the NFC and this was a sequel to another devastating playoff loss to Green Bay that we’ll touch on shortly.

3. Giants 21, Cowboys 17 – Divisional Round 2007 playoffs

There are three reasons this loss hurt a little extra for Cowboys fans.

First, Dallas had a 13-3 record and was the top seed in the NFC. This also matched the franchise record for most wins in a season. It was the Cowboys best shot at winning a Super Bowl in a long time.

Second, extra salt was added to the wound, considering an NFC East rival came to Dallas and got the victory. New York was 10-6 on the year and snuck into the second wild card spot. But the Cowboys won both regular season games against New York, so Dallas fans had good reason to be confident.

Lastly, during the first round playoff bye, Tony Romo and other Cowboys players vacationed in Cabo San Lucas with the QB and his now ex-girlfriend Jessica Simpson. Naturally, this drummed up lots of discussion about how seriously Dallas was taking the postseason and if their time could’ve been better spent practicing. Apparently, it couldn’t have hurt to get the extra reps in.

2. Seahawks 21, Cowboys 20 – Wild Card Round 2006 playoffs

The 2006 Cowboys weren’t as dominant as some other teams we’ve seen since 2000. It was Romo’s first year taking over starting QB duties, and he played well enough to sneak the 9-7 Cowboys into the last spot for the playoffs.

It was a back-and-forth game that had five lead changes. With 1:19 left in the fourth quarter, Dallas trailed by a point before veteran kicker Martin Garamatica trotted out to attempt a 19-yard field goal.

But Romo, who also served as the placeholder, fumbled the snap and tried scampering to the outside to sneak into the endzone. For a second, it looked like he might make it in before he was tripped up by a Seattle defender.

From that game, Cowboys fans learned nothing in life is certain until it actually happens, especially 19-yard field goals. They also spent many sleepless nights staring at their bedroom ceilings, wondering why the hell Romo was the placeholder to begin with.

1. Packers 26, Cowboys 21 – Divisional Round 2014 playoffs

This game featured the dreaded play that has fans debating to this day: ‘Did Dez catch it?’. 

In the regular season, Dallas boasted a high-powered offense led by Romo, DeMarco Murray and Dez Bryant. It’s not often a team’s QB, RB and WR all earn Pro Bowl selections, but that’s how much talent the Cowboys had that year. Murray and Bryant also earned All-Pro honors.

Dallas held a 12-4 record as a team, had the fifth highest points per game average at 29.2 and were NFC East champions.

But things went sideways in the postseason against Green Bay. Let’s set the scene: it’s the fourth quarter and the Cowboys are trailing 26-21. With 4:42 left in the game, Dallas needs to gain two yards to convert a fourth down and keep moving the ball towards the end zone, as they’re already on the Packers 32 yard line.

Rather than run the ball or throw it short, Romo went downfield to Bryant who made a contested catch before falling on the one yard line. The ball did squirt loose at the end of the catch, but Bryant clearly caught it and took two steps before going down. The commentators thought it was a catch, the players thought it was a catch, the fans thought it was a catch, if you were watching the game live, you probably thought it was a catch, etc. 

But then-Green Bay coach Mike McCarthy threw the challenge flag and it was successful. The Cowboys turned the ball over on downs and the Packers were able to run the clock out. This would alter the NFL’s officiating future, as refs and fans alike dealt with new rules from the league constituting the various factors going into catching a pass, like making a football move.

To this day, Dallas fans daydream about how things might’ve gone if the refs didn’t overturn the play.