Tony Romo's 10 most heartbreaking losses

Dallas Cowboys owner Jerry Jones called Sunday's insane loss to the Green Bay Packers one of the "hardest losses that I've experienced."

He has plenty of options to choose from. The Jason Garrett-Tony Romo era has produced a string of ridiculous losses, each one seemingly more excruciating than the one before. The Cowboys don't just blow big leads; they blow 23-point leads to Matt Flynn on five successive touchdown drives, with two Tony Romo interceptions in the final four minutes mixed in.

Sunday's meltdown got us thinking about where this game would rank on the list of the most heartbreaking losses of Romo's career. Here are 10 that come to mind, with a lot of help from our video department.

10. October 27, 2013: Last-second loss to Detroit

Dallas blows a 10-point lead in the fourth quarter and gives up an 80-yard touchdown drive with one minute left to lose to Matthew Stafford and the gang.

9. September 12, 2011: Week 1 loss to the Jets

In Romo's first game back from a broken collarbone, the Cowboys coughed up a 14-point fourth-quarter lead. It was highlighted by Romo's late fumble on the goal line and an interception to Darrelle Revis in a tie game with under one minute left.

8. October 28, 2012: Dez Bryant's near miracle

Just when you think the Cowboys are going to win one of these bonkers endings, the officials ruin it.

7. December 7, 2008: Week 14 loss to Pittsburgh

Pittsburgh scores 17 unanswered points in the fourth quarter, capped off by Deshea Townsend's game-winning pick six of Romo. This kick starts a December swoon that leaves Dallas out of the playoffs.

6. October 6, 2013: 51-48 loss to Denver

This was the ultimate Romo debate Rorschach test. Romo threw for more than 500 yards with five touchdown passes, but a late interception spoiled the day. Jerry Jones said it was Romo's best game as a pro. That felt true, but so strange to say after another crushing loss.

5. December 12, 2011: Lost in the lights

Miles Austin loses a potential NFC East-winning pass in the lights, Jason Pierre-Paul blocks a field goal and the Giants end a four-game losing streak. The Giants go on to win the division and the Super Bowl.

Bonus points for this video starting with the words, "Tony Romo and company trying to forget that awful ending in Arizona."

(That one was a beauty, too.)

4. December 15, 2013: 23-point collapse against Green Bay

If the Cowboys have turned heartbreak into an art form, this was their Sistine Chapel.

3. January 6, 2007: Wild-card loss to Seattle

Tony Romo's botched field-goal hold ruins his once-magical first season as a starter. The Cowboys lost their final three games of the season. This one would rank first on our "Unfair to blame Romo" game rankings. It also was the final game of Bill Parcells' coaching career.

2. December 30, 2012: Division decider against Redskins (and the rest of the Week 17 disasters.)

Romo throws three interceptions in a Week 17 play-in game to decide the NFC East championship. This spot stands symbolically for all of the Week 17 losses that decided the NFC East, like the 31-14 loss to New York at the end of the 2011 season and the 44-6 loss to Philadelphia to end the 2008 season.

1. January 13, 2008: Divisional Round loss to New York

This was supposed to be the Cowboys' Super Bowl year, but the NFC's No. 1 seed fell in a nail-biter to its division rivals. A huge Patrick Crayton drop in the third quarter is forgotten. Romo's game-ending pick and Terrell Owens' tearful "That's my quarterback" sound bite live on.

*The latest "Around The League Podcast" broke down the Cowboys' loss and every other Week 15 game. *