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5 Most Heartbreaking Losses Of The Tony Romo Era

As we all know by now the lost an absolute heartbreaker to their bitter East rivals, the , in a primetime game at Jerry World with future playoff implications on Sunday night. I think I speak for all of when I say, “at the time, I can't remember a game that hurt as badly as this one did.”

Jerry World, Philadelphia Eagles, heartbreaker, and loss.

That's just plain and simply the worst, and on top of that, Eagles fans act like they've never won a game before.

However, after watching go over the goal line, run past and chuck the ball up into Cowboys Nation while it seemed like thousands of Eagles fans roared in glee, it's clear it wasn't the first time we've seen a narrative similar to this one before.

That brings me to a guy whose name not only brings joy to our lives whenever we hear it but also sounds like the owner of your local Italian restaurant. Antonio Ramiro Romo. Miss him yet, Cowboys Nation?

[youtube https://www.youtube.com/watch?v=wU6EnQMWc4M]

How about now?

Yeah, I do too. But while should go down as one of the most clutch Quarterbacks this league has ever seen, he also will go down as the responsible for some absolutely gut wrenching and heartbreaking losses over the years.

We at figured it would be a great time to rank the top 5 most heartbreaking losses of the Tony Romo era because this is as low as it's been in years for Cowboys Nation. While reliving these moments will be hard for all us, this will make watching Tony Romo and our Boys finally hoisting that Lombardi trophy over their heads that much more bittersweet.

So let's get this over with…

New York Giants @ Dallas Cowboys 12/12/2011 – Week 14

Well, this one was brutal, and against and the Giants no less.

The Cowboys had 2 things go their way in this one and that was bringing in a great interception and Mario Manningham dropping that ball. Aside from that, it was the Giants getting some dumb luck and Eli Manning chucking up prayers off his back foot to convert a critical 3rd and 1.

Oh and dancing like an absolute dunce on the star was chill.

Highlights:

http://www.nfl.com/videos/nfl-game-highlights/09000d5d824f8893/GameDay-Giants-vs-Cowboys-highlights

 

Washington Redskins v. Dallas Cowboys 12/30/2012 – Week 17

Of all of the debacles the Dallas Cowboys had over the years, this one is by far the worst and most heartbreaking. RGIII running in for a score, Dan Snyder cheering in his skybox like a buffoon, Dez walking gingerly off the field, and Romo throwing that gross interception late were all equally cringeworthy.

Tough to top this one, but alas there are 3 more that are easily worse.

Highlights:

http://www.nfl.com/videos/nfl-network-gameday/0ap2000000119790/GameDay-Cowboys-vs-Redskins-highlights

 

Green Bay Packers v. Dallas Cowboys 1/11/2015 – NFC Divisional Playoffs

Dez caught it.

Highlights:

http://www.nfl.com/videos/nfl-network-gameday/0ap3000000456807/Divisional-Round-Cowboys-vs-Packers-highlights

 

Seattle Seahawks v. Dallas Cowboys 1/6/2007 – NFC Wild Card Playoffs

I remember watching only the second half of this one at a friends house fresh off of a hockey tournament game I had played earlier that evening. I have been a Cowboys fan since day 1 Cowboys Nation, but this game right here was where I really grew close to the team that I love and I'm sure some of the younger fans are right with me.

This one speaks for itself, though, and anyone who has followed the NFL or hated the Cowboys knows what happens in this one. I'll let the highlights speak for themselves.

Highlights:

http://www.nfl.com/videos/nfl-game-highlights/0ap2000000274664/GameDay-Cowboys-vs-Seahawks

Good thing Martin Gramatica laid a key block.

 

New York Giants @ Dallas Cowboys 1/13/2008 – NFC Divisional Playoffs

I know this list may cause some controversy, but this is by far the most heartbreaking loss the Dallas Cowboys have suffered on Tony Romo's watch – hands down.

Die hards of Cowboys Nation know that this was supposed to be “our year.” The Giants were just the little kid with an ice cream cone at the beach on a hot day, and the Cowboys were one of the O'Doyle brothers just passing by.

Just one year removed from the terrible heartbreak the Seahawks handed the Boys, this just pushed the stake in our hearts even further.

Highlights:

http://www.nfl.com/videos/nfl-game-highlights/0ap2000000274661/GameDay-Giants-vs-Cowboys

That wasn't so hard was it, Cowboys Nation? Ok, yes, it was. But you know what? One day the Dallas Cowboys are going to raise that Lombardi Trophy over their heads in victory once again and we are going to look back at all of these moments and just smirk.

You wanna know what else?

Antonio Ramiro Romo is going to be the first to raise it.

Harry Brockman
Harry Brockman
Former hockey player from Orlando Florida who has an unprecedented desire to write and talk about sports every single day. The Dallas Cowboys were my first love in sports and I continue that relationship to this day. Hit me up on Twitter! @H_Brock7 #InRomoWeTrust

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