Top 5 Worst Moments of Tony Romo's Career

While he may have rallied through broken ribs and a punctured lung to victory against the San Francisco 49ers, Tony Romo has had many less than stellar moments in his career. He has had multiple dating fiascos, only one playoff win and run ins with teammates.

So when counting down the best of the worst, the real question is whether to start off with Jessica Simpson, or end with her the way Romo and his season did.

Terrell Owens Drama

It was a joint concern between T.O., Roy Williams and Patrick Crayton when Romo was blowing up Jason Witten on the field back in 2008.  We all know how T.O. can be, and it was probably a mix of him being jealous and being a drama queen. However, it did get to the point that Romo wouldn't talk about Owens in interviews.

Good Ole Jessica Simpson

It all started when Jessica Simpson showed up to a Cowboys game in a pink No. 9 jersey, and went seriously downhill from there.  The romance was well publicized up until he broke up with her right before her birthday.

Fans taunted Romo in playoff games with pictures of Jessica in the stands, it worked out pretty well for the opposing teams.

Who Needs Playoffs When You Have Cabo San Lucas and a Pair of Sticks?

Tony Romo plays enough golf to join the PGA and visits Cabo San Lucas like he was a member of Laguna Beach.  His worst strike? Taking dear Jessica to Cabo the week of a playoff game.  All that R & R failed to give the expected result when he came back and lost his game.

2007 Playoffs

In their devastating 21-20 loss to the Seattle Seahawks in the 2007 playoffs, Tony Romo fumbled the potential game-winning 10-yard field goal snap. Was this perhaps the reason Bill Parcells retired after that season?

2008 Playoffs

Yet another Playoff party foul on Tony Romo's behalf. With :09 seconds left in the game, Romo threw an interception allowing the Giants to defeat the Cowboys.  That was the first time in 20 years that the No. 1 seed had been knocked out in the divisional round of the playoffs. Hats off to Tony.