Dallas Cowboys quarterback Tony Romo (9) is touch down by New Orleans Saints outside linebacker Kasim Edebali (91) after a fumble during a regular season NFL football game between the Dallas Cowboys and the New Orleans Saints at AT&T Stadium in Arlington, TX. Cowboys won 38-17.
Ray Carlin/Icon Sportswire/Corbis/Icon Sportswire via Getty Images
At one point, the Dallas Cowboys were tied with the San Francisco 49ers as the franchises with the most Super Bowl victories. Both have since dropped to second place, but Big D fans have endured three decades of sorrow since their last Super Bowl championship.
January 28, 1996, was the last day the Dallas Cowboys appeared in the Super Bowl, let alone won the trophy. Division rivals Philadelphia Eagles and New York Giants have both won two Super Bowls in the three decades since. For Cowboys fans, the past three decades have brought only missed opportunities, wasted talent and playoff heartbreak.
Article continues below this ad
So, in honor of the new season, let’s look back at the Cowboys’ 30 worst moments in the 30 years since their last Super Bowl victory.
Dez Bryant catch vs. Green Bay
Dez Bryant’s “incomplete” catch against Green Bay in 2014 remains the closest the team has come to the NFC Championship Game since 1995.
Article continues below this ad
Tony Romo botched hold vs. Seattle
Tony Romo fumbled the snap while holding for the kicker during the 2006 Wild Card, letting Seattle escape with a 21-20 win in hilarious fashion.
Article continues below this ad
Dallas Goedert draft day in Dallas
A player named Dallas, drafted in the Dallas area by the Philadelphia Eagles in 2018, let David Akers’ epic trolling: “Hey Dallas, the last time you were in the Super Bowl, these draft picks weren’t born.”
Ezekiel Elliott pancake
Azeez Al-Shaair pancaking Ezekiel Elliott on the last play of the 2023 Divisional Round stands as the lowest of low moments for a player who was one time one of the best running backs in the league.
Article continues below this ad
Barry Switzer coaching failures
Three-time national champion Barry Switzer may have won Super Bowl XXX with the Cowboys, but his struggles leading the NFL saw Dallas’ further potential wasted in the late 90s.
Three-straight 8-8 seasons
The struggles of the last 30 years were on full display from 2011 to 2013 when the Cowboys went 8-8 for three straight seasons. Each season, the Cowboys could’ve made the playoffs but lost in the final weeks.
Article continues below this ad
Insulting DeMarco Murray
DeMarco Murray set the Cowboys’ single-season rushing record (1,845 yards) in 2014 but was not re-signed by the team. Seeing how well Ezekiel Elliott played as a rookie behind Dallas’ offensive line, Murray remains a major what-if in NFL history.
Losing to Colt McCoy
The Washington Redskins went 4-12 in 2014, but one of those wins was a 20-17 overtime win at Dallas. The game was noted for being Texas Longhorns legend Colt McCoy’s first NFL game back in Texas. The local kid won the day, but the hometown suffered.
Article continues below this ad
Joseph Randle legal trouble
Joseph Randle looked like he’d taken over the Cowboys’ running back role through the first six games of the 2015 season, highlighted by a three-touchdown game against the Atlanta Falcons. However, he went on to be waived by the Cowboys before a league suspension and has faced legal troubles ever since, most notably accusations of rape in 2018.
Joey Galloway #84 of the Dallas Cowboys sits near the medical station with an injury that removes him from the rest of the football season during the game against the Philadelphia Eagles at the Texas Stadium in Irving, Texas. The Eagles defeated the Cowboys 41-14.
Ronald Martinez/Getty Images
Joey Galloway trade bust
Wide receiver Joey Galloway had five productive years with the Seattle Seahawks when the Cowboys traded for him in 2000. Dallas gave up two first-round draft picks for Galloway, but over four seasons he never recorded 1,000 receiving yards.
Article continues below this ad
Quincy Carter draft bust
The Galloway trade meant Dallas didn’t have a first-round draft pick in 2001. Needing a quarterback after Troy Aikman’s retirement in 2000, the Cowboys missed out on Drew Brees and ended up with Georgia’s Quincy Carter. Despite being a star in college, Carter struggled in three years with Dallas. The team reached the 2003 playoffs, but Carter was cut after a 29-10 Wild Card loss to Carolina.
Roy Williams (11) of the Dallas Cowboys during the Cowboys 20-8 win over the New York Giants at Texas Stadium in Irving, Texas.
James D. Smith /Icon SMI/Icon Sport Media via Getty Images
Roy Williams trade bust
Former Texas Longhorns star Roy Williams began his NFL career with the Detroit Lions, but Dallas traded for him in 2008 to boost its wide receiver corps. Unfortunately, he never caught 600 yards in a single season and was cut after Dez Bryant emerged.
Article continues below this ad
Losing to Houston Texans in their very first game
Another dark day in Cowboys history was September 8, 2002. The Cowboys were the first opponent of the newly franchised Houston Texans. Despite all their championship history, the Cowboys lost to the newcomers 19-10 to give Houston its first-ever win.
TO posing on the Dallas Star
On September 24, 2000, Terrell “TO” Owens trolled the Cowboys by scoring two touchdowns, celebrating in the middle of the field and causing a fight to break out. San Francisco won 41-24.
Article continues below this ad
Texas Stadium demolition
The Cowboys won all five Super Bowls in the Texas Stadium era in Irving. The stadium was demolished in 2010 after AT&T Stadium opened. The new stadium hasn’t added any luck to the Cowboys’ championship dreams. Coincidence? Maybe, maybe not.
Micah Parsons trade
At 26 years old, the former Defensive Rookie of the Year was the clear leader on the Cowboys’ defense when Jerry Jones traded him to a loaded Packers team without an equal star in return. The move still confuses Cowboys fans.
Article continues below this ad
Not drafting Randy Moss
Hall of Famer Randy Moss grew up wanting to play for Dallas. When the Cowboys passed on him, he torched them on Thanksgiving Day 1998 with three catches for 163 yards and three touchdowns.
Tony Pollard #20 of the Dallas Cowboys celebrates a touchdown against the Chicago Bears during the second quarter at AT&T Stadium on October 30, 2022 in Arlington, Texas.
Richard Rodriguez/Getty Images
Not re-signing Tony Pollard
Tony Pollard has rushed for four straight 1,000-yard seasons. However, after back-to-back 1,000-yard seasons in 2022 and 2023, the Cowboys let him walk to the Tennessee Titans, abandoning whatever progress they’d made.
Article continues below this ad
DeMarcus Lawrence (left) and DeMarcus Ware (far right) during their time with the Dallas Cowboys.
Getty Images
Wasting DeMarcus Ware and DeMarcus Lawrence’s prime
DeMarcus Ware and DeMarcus Lawrence both were decade-long defensive stars in Dallas. Neither of them won Super Bowls until they left for Denver and Seattle, respectively.
Loss to Giants in 2007 playoffs
Tony Romo’s breakout season came in 2007 when he led the Cowboys to a 13-3 record and the No. 1 seed in the NFC. However, the championship dreams came crashing down in the Divisional Round with a 21-17 loss to eventual champions New York Giants.
Article continues below this ad
Packers embarrass Cowboys at home, twice
The Packers defeated Dallas in Green Bay in 2014 and then knocked off the Cowboys at home in 2016 and 2023, the latter being a 48-32 blowout. It’s the last time the Cowboys made the playoffs.
Lions 47, Cowboys 9
The Detroit Lions completely embarrassed the Cowboys with a 47-9 victory on October 13, 2024. The loss stands as the fourth-worst in Cowboys history and the largest defeat at AT&T Stadium.
Article continues below this ad
Drafting Taco Charlton over T.J. Watt
Dallas could’ve had T.J. Watt in the 2017 NFL Draft. They instead chose Taco Charlton out of Michigan. Watt went on to become Defensive Player of the Year in 2021, while Charlton was out of Dallas after two seasons.
Signing Greg Hardy
The Cowboys were rightly shamed for signing Greg Hardy in 2015. The defensive end was a star in Carolina, but Dallas deservedly caught heat for a man convicted on domestic violence charges.
Article continues below this ad
Dak Prescott playoff-losing scramble
Dak Prescott scrambling for a first down but not leaving enough time to spike the ball led to an embarrassing loss to the San Francisco 49ers in the 2021 Wild Card Round.
Josh Brent DUI car crash, Jerry Brown death
Defensive tackle Josh Brent was convicted of intoxication manslaughter in 2012 after a DWI crash caused the death of teammate Jerry Brown. He served 180 days in jail and 10 years’ probation.
Article continues below this ad
Michael Irvin’s cocaine bust in 1996
In 1996, Michael Irvin was indicted on felony cocaine-possession charges after police found him, former teammate Alfredo Roberts and two women in an Irving motel room where they also found cocaine, marijuana and drug paraphernalia, according to the Roanoke Times. Irvin later pleaded no contest to felony cocaine possession and received deferred probation
Jalen Hurts #1 of the Philadelphia Eagles celebrates with the Vince Lombardi Trophy after defeating the Kansas City Chiefs 40-22 to win Super Bowl LIX at Caesars Superdome on February 09, 2025 in New Orleans, Louisiana.
Jamie Squire/Getty Images
Philadelphia Eagles Super Bowl victories
The greatest salt in the wound for Cowboys fans. The Philadelphia Eagles have advanced to four Super Bowls and won two in the 30 years since the Cowboys last made the Sunday classic.
Article continues below this ad
Trevon Diggs fallout
Trevon Diggs looked like he’d be a defensive star with the Cowboys for years to come when he had 11 interceptions in 2021, the most for the team in 40 years. However, Diggs managed only four interceptions over the next four seasons, and his declining numbers led to his release at the end of the 2025 season.
Article continues below this ad
Odell Beckham Jr. one-handed catch
CeeDee Lamb #88 of the Dallas Cowboys is tackled by Keisean Nixon #25 of the Green Bay Packers and Jaire Alexander #23 of the Green Bay Packers during an NFL wild-card playoff football game between the Dallas Cowboys and the Green Bay Packers at AT&T Stadium on January 14, 2024 in Arlington, Texas.
Michael Owens/Getty Images
DeMarcus Lawrence #90 of the Dallas Cowboys celebrates during an NFL wild-card playoff football game against the Green Bay Packers at AT&T Stadium on January 14, 2024 in Arlington, Texas.
Perry Knotts/Getty Images
DeMarcus Ware #94 and Morris Claiborne #24 of the Dallas Cowboys celebrate in the second half against the Philadelphia Eagles at Cowboys Stadium on December 29, 2013 in Arlington, Texas.
Ronald Martinez/Getty Images
Odell Beckham Jr. will forever be remembered for his falling-down, one-handed catch from his rookie year. The team he was playing against? The Dallas Cowboys.