The top 5 most painful losses in Dallas Cowboys history

2. 2007 Divisional loss to the Giants – A season full of drama

After a disappointing end to the 2006 season, the Cowboys (led by up-and-coming QB Tony Romo) burst onto the scene, going 13-3 and locking up the No. 1 seed and the first-round bye. Behind Romo’s 36 touchdowns, the Cowboys offense was lethal. With several talented skill players, like Hall of Famer Terrell Owens, Dallas looked poised and ready to make it to the Super Bowl. However, fate had other plans.

Before the divisional round matchup against the Giants, the Cowboys would become a media circus. At the time, Romo was dating singer Jessica Simpson, causing the rising star to garner far too much attention and scrutiny. When No. 9 and other Cowboys players decided to join Simpson on a vacation to Cabo San Lucas during the bye week before the big game, the criticism of this decision grew to tremendous levels.

While many thought Dallas would destroy the Giants, like they had done twice earlier in the year, the Cowboys were not ready for what this game had in store for them.

This was a game the Cowboys should’ve had in hand; however, they lost the game more than the Giants won the game. Several mistakes ruined the Cowboys’ chances at getting the Conference Championship for the first time since the 90s.

Having to settle for a field goal because of a dropped touchdown pass attempt to Anthony Fasano, made the game 17-14. Then, they punted on the next drive due to a Patrick Crayton dropped pass that could’ve gone all the way. This gave the Giants great field position and they ultimately took a 21-17 lead.

Dallas was given a chance to overcome the flaws, though.  With 1:50 left on the clock, Romo marched down to the Giants’ 23-yard line with only 21 seconds left in the game. It was 3rd and 11, and Romo looked Patrick Crayton’s way again in the back of the endzone on what looked to be a perfectly placed ball.

For some unknown reason, Crayton stopped running and the ball fell incomplete. Instead of easily winning the game there, it was fourth down and Romo was forced to attempt a desperate heave into the endzone into double coverage where the ball got intercepted.

This one was excruciating. That’s the best way to describe it. This may be, perhaps to this day, the best Cowboys team to not win it all. This would be the game that would create Romo’s brand as a choker. He would go on to be the most disputed figure in football as the Cowboys would inevitably fall flat year after year. But nothing was as bad as the next game.