Best and worst Cowboys seasons, plus most disappointing finishes, since their last Super Bowl win

The Dallas Cowboys are preparing for another reset after parting with head coach Mike McCarthy last week.

While that’s something team owner Jerry Jones has done plenty of times in the past, he still hasn’t managed to make it back to the Super Bowl, let alone an NFC title game, in nearly three decades now despite appearing to — at least on paper — have teams capable of that feat at his disposal.

Now, he’s watching two recent assistants, Commanders head coach Dan Quinn and Eagles offensive coordinator Kellen Moore, square off in the NFC title game for the right to go to the Super Bowl. The Commanders’ rise to the conference title game made the Cowboys the franchise with the longest NFC title game drought, which dates back to the 1995 season.

Brian Schottenheimer has become the betting favorite to earn the job. Here’s a look at the latest on the Cowboys’ coaching job front.

As Dallas’ coaching search continues, here’s a look back at some of the best seasons, worst seasons and brutal finishes in the Cowboys’ 29 years since their win in Super Bowl XXX.

Last Cowboys Super Bowl win: 1995 season

Record: 12-4

NFC East finish: 1st

Playoffs: Super Bowl

The Cowboys beat the Pittsburgh Steelers in the Super Bowl, which marked their third championship in a four-year stretch under the Triplets of quarterback Troy Aikman, running back Emmitt Smith and wide receiver Michael Irvin. They have not been to the Super Bowl, or even the NFC championship game, since.

Best seasons

1996

Record: 10-6

NFC East finish: 1st

Playoffs: Divisional round

On the heels of their Super Bowl win, Aikman and Smith got the Cowboys back to the playoffs for a sixth straight campaign after running through the NFC East. They blew out the Vikings in the first round of the playoffs before getting eliminated in the next round by the Panthers.

This undoubtedly marked the end of their dynasty, although these Cowboys put together one good last run.

2007

Record: 13-3

NFC East finish: 1st

Playoffs: Divisional round

After their 2006 finish (we’ll get to that), the Cowboys responded the following season to claim their first NFC East title in nearly a decade. They racked up 13 wins, which is something the team hadn’t seen since 1992, under first-year head coach Wade Phillips and claimed the top seed in the NFC.

But the Cowboys fell in the divisional round to the eventual Super Bowl champion New York Giants. This was a great Cowboys season that resulted in nothing come playoff time.

2016

Record: 13-3

NFC East finish: 1st

Playoffs: Divisional round

After losing Tony Romo to injury the year before, Dak Prescott stepped in during his rookie season and led the Cowboys to their best finish in nearly a decade. They earned the No. 1 seed in the NFC and second NFC East title in three years. But Aaron Rodgers got the Cowboys in the playoffs to cut their season short.

Worst seasons

2000-2002

Record: 5-11, 5-11, 5-11

NFC East finish: 4th, 5th, 4th

Playoffs: No

We’ve lumped these three seasons together because, well, they were shockingly similar with how underwhelming they were. The Cowboys went 5-11 in three straight campaigns under head coach Dave Campo, who was fired after the 2002 season. They did not make the playoffs once, and struggled to find their footing at the end of the Aikman era in Dallas. It was a whole lot of nothing.

As far as bad stretches go for the Cowboys, this one is up there.

2015

Record: 4-12

NFC East finish: 4th

Playoffs: No

There is a lot that went wrong during this campaign. The Cowboys won just four games the entire season, which was their lowest win total since the 1989 season when they went 1-15. They even started 2-0 with divisional wins, which made the finish even worse. Romo went down with a broken collarbone in the second game of the season, star wide receiver Dez Bryant battled a broken foot and everything spiraled after that.

2024

Record: 7-10

NFC East finish: 3rd

Playoffs: No

There may be a bit of recency bias here, but this past season was among the worst for the Cowboys in recent decades. They lost Prescott to a season-ending injury, missed the playoffs for the first time since the 2020 season and sustained multiple blowout losses throughout the campaign. Oh, and it resulted in them parting with McCarthy. Not great.

Most disappointing finishes

2006

Record: 9-7

NFC East finish: 2nd

Playoffs: Wild-card round

Nothing about this season, the final one under head coach Bill Parcells, was that special. But a brutal loss in the playoffs makes it stand out.

With about 80 seconds left in their wild-card matchup against the Seattle Seahawks, Romo came out to hold a 19-yard field-goal attempt that would’ve put Dallas ahead. Romo, who took over as the team’s starter that season, still maintained his holding job throughout the season. But Romo fumbled the snap.

Instead of going down in the backfield, Romo somehow scooped up the fumble and swung around to the outside to find what looked like a clear path to the end zone. At the last second, he was brought down inches shy of a first down. Romo’s hand was left bloodied after it was stepped on.

It’s unclear how far this Cowboys team was capable of making it in the postseason that year, but the finish was undoubtedly heartbreaking.

2014

Record: 12-4

NFC East finish: 1st

Playoffs: Divisional round

This Romo-led Cowboys team was great. They made it back to the playoffs for the first time in the decade. But the finish at Lambeau Field is the highlight the season is remembered for.

Near the end of their divisional-round playoff game, Romo threw a deep pass to Dez Bryant that appeared to be caught but was later overturned on replay. The play would’ve put the Cowboys in position to score and take the lead late. Instead, the Packers ended up winning and the “Dez Caught It” lore was born. This play sparked a debate about what a catch actually is in the NFL for years.

2021

Record: 12-5

NFC East finish: 1st

Playoffs: Wild-card round

After a pair of bad seasons, including the first under McCarthy, the Cowboys erupted in 2021 with the trio of Prescott, Ezekiel Elliott and CeeDee Lamb. They won their first NFC East title since the 2018 season and set up a home playoff game. Despite going 6-0 against their division and winning five of their last six games, the Cowboys fell flat in the playoffs.

After nearly leading Dallas on a game-winning drive, Prescott scrambled up the middle of the field and slid to give himself up. Despite putting the Cowboys in great field position, he ended up not having enough time to run another play. While this isn’t as rough as the other two on this list, it was another example of the Cowboys coming up short in clutch time.