The short answer is no. Tony Romo never won a Super Bowl.
If you’re a Dallas Cowboys fan, just reading those words probably stings a little. Romo is one of the most polarizing figures in modern NFL history. On one hand, you have a guy who went from being an undrafted free agent out of Eastern Illinois to holding almost every major passing record for the most valuable sports franchise on the planet. On the other, he’s the face of a decade-long era where the Cowboys consistently "almost" had it, but never quite got over the hump.
He finished his career with zero rings and zero Super Bowl appearances. Honestly, he never even made it to an NFC Championship game.
Did Tony Romo win a Super Bowl? Breaking down the postseason reality
Despite the lack of hardware, Romo wasn't exactly a "bad" playoff performer by the numbers. He played in six postseason games, starting four of them (he was the holder/backup for others early on). He finished his playoff career with 8 touchdowns, only 2 interceptions, and a 93.0 passer rating. For context, that’s a better postseason rating than many Hall of Famers.
So why the "choker" label?
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It basically boils down to a few high-profile moments where things went sideways in the most public way possible. Because he wore the star on his helmet, every mistake was magnified by ten.
The 2006 Botched Snap
The first big scar was the 2006 Wild Card game against the Seattle Seahawks. Romo was the holder for a potential game-winning 19-yard field goal. The snap was perfect, but Romo fumbled the ball while trying to set it down. He tried to scramble for the end zone, got tackled short, and the Cowboys lost. It was a freak accident, but it set a narrative that he could never quite shake.
The 2014 "Dez Caught It" Game
This was probably Romo’s best chance. The 2014 Cowboys were a juggernaut. Romo led the league in passer rating (113.2) and completion percentage (69.9%) that year. In the Divisional Round against the Green Bay Packers, he threw a perfect deep ball to Dez Bryant on 4th-and-2.
Dez caught it. Then he didn't.
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According to the rules at the time, it was ruled an incomplete pass. The Cowboys lost 34-31. If that catch stands, there’s a very real world where Romo has a ring today.
Why the Super Bowl remained out of reach
Winning in the NFL is a team sport, and Romo often had to carry some pretty lopsided rosters. Throughout the early 2010s, the Cowboys’ defense was, frankly, a mess. In 2013, Romo threw for 506 yards and 5 touchdowns against Peyton Manning and the Broncos, only to lose 51-48 because the defense couldn't get a single stop.
Critics point to his 2-4 record as a starter in the playoffs. Supporters point to the fact that he retired with a career passer rating of 97.1—which, at the time of his retirement, was the fourth-highest in NFL history.
A Career of "What Ifs"
- 2007: The Cowboys were the #1 seed but lost to the Giants (who went on to win the Super Bowl).
- 2009: They finally won a playoff game against the Eagles, but got demolished by Brett Favre and the Vikings the following week.
- Injuries: By the time the Cowboys finally built an elite offensive line in 2015 and 2016, Romo’s body was breaking down. He suffered multiple back fractures and a broken collarbone, eventually losing his job to rookie Dak Prescott.
The transition to the broadcast booth
While he didn't win a Super Bowl as a player, Romo has called three of them as a broadcaster for CBS (Super Bowls LIII, LV, and LVIII). It’s a bit of a cruel irony. He became a superstar in the booth almost instantly, known for his "Romo-stradamus" ability to predict plays before they happened.
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Even now, in 2026, fans still debate his legacy. Was he a great quarterback who was failed by his team, or a "stats guy" who lacked the "it" factor when the lights were brightest?
Actionable insights for fans and collectors
If you're looking into Tony Romo's career from a historical or memorabilia perspective, keep these facts in mind:
- Records: He still holds the Cowboys' all-time records for passing yards (34,183) and passing touchdowns (248), even though Dak Prescott is closing in.
- Efficiency: Don't let the "choker" narrative fool you. His career 7.9 yards per attempt is elite, ranking him among the most efficient passers to ever play.
- Memorabilia Value: Because he never won a ring, Romo’s rookie cards and signed jerseys often trade at a significant discount compared to guys like Eli Manning or Drew Brees, despite Romo having comparable (or better) regular-season stats. This makes him a "buy low" candidate for fans who appreciate the era.
Ultimately, Tony Romo’s career is a reminder that the Super Bowl is the ultimate measuring stick, even if it doesn't tell the whole story of a player's talent. He was an undrafted kid who became a legend, and while the trophy case is empty, his impact on the game—both on the field and in the booth—is undeniable.