There were plenty of great moments during his time in Dallas, from his win over the Lions in the playoffs a few years ago to beating the 49ers with a punctured lung, but there were also low points.
As great as Romo was, his heartbreaking defeats will be remembered for a long time. Here are his five worst moments with the Cowboys.
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A 44-6 loss to the Eagles in Week 17 of 2008
The Cowboys needed to beat their division rival Eagles in Week 17 in order to get into the playoffs. Romo had been playing fairly well, but Dallas lost two of its last three and was in danger of missing the postseason. Needless to say, the game didn’t go as planned.
Romo completed just 21 of 39 passes for 183 yards with no touchdowns and three interceptions as the Cowboys were blown out of the water by the Eagles, 44-6. It was the second-worst performance of Romo’s season with a putrid passer rating of 55.8.
After making the playoffs in back-to-back years, this was a huge letdown for a Cowboys team that should have made the playoffs.
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2012 Week 17 loss to Redskins with the NFC East title up for grabs
Romo has always been criticized for being bad in big situations, and this game is one of the biggest reasons for that. Three times Romo lost a Week 17 game that would have gotten Dallas into the playoffs with a win. The worst of them all came in 2012, when he threw three interceptions against the Redskins, ending the Cowboys’ season with heartbreak and disappointment.
His terrible interception with the Cowboys trailing 21-18 and just over three minutes to play was the one that did him in, essentially clinching the win for Washington. The Redskins would turn the pick into a touchdown and knock off the Cowboys 28-18.
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Losing to the Giants in the 2007 Divisional Round
The Cowboys were the favorites to win it all in 2007. They went 13-3, had the No. 1 seed and a first-round bye, setting up a potentially deep run in the postseason. Unfortunately, they ran into the Giants in the Divisional Round, ending their season a few weeks earlier than they had hoped.
That came after Romo and Jason Witten spent their bye week vacationing in Cabo, which made the loss even more difficult to swallow as the Cowboys faced similar questions to the ones the Giants got this past season for their boat trip in Miami.
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The straw that broke Romo’s back
The Romo era in Dallas came to an abrupt and surprising end in the preseason last year. He suffered a back injury against the Seahawks in a meaningless preseason game, thus keeping him out for most of the year.
The injury gave way to Dak Prescott as the starter, and the rookie never looked back. Romo threw just four more passes and one touchdown in his career with the Cowboys, playing one series against the Eagles in Week 17.
Had it not been for the unfortunate injury, Romo likely would have been the starter for all of 2016, and potentially many years to come. Sadly, that’s just the way the NFL works, where one injury can end an era and give way to a new one.
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Botched hold vs. Seahawks in 2007
There's no doubt about this one being Romo’s worst moment in Dallas. In his first season as the Cowboys’ starter, Romo was still the holder on field goals. Needing a chip-shot 19-yard attempt from Martin Gramatica to go ahead by two points with just over a minute remaining, all Romo had to do was get the snap down. Gramatica likely would have drilled it and sent the Cowboys to the next round, but we all know what happened instead.
The snap slipped through Romo’s hands as he raced to the end zone, only to come up a couple yards short. He faced an overwhelming amount of scrutiny afterward, forcing him to overcome the biggest mistake of his career for years to come.