The Philadelphia Eagles have a long history in the NFL. In that time, they've had some wonderful moments.

Moments that defined the franchise, thrilling moments like winning the Super Bowl or the “Miracle at the Meadowlands II”. There are so many great moments to choose from, it's hard to pick the best.

That being said, there is the opposite side of that coin. There are those heartbreaking moments too. And as any fan of the Eagles would probably tell you, they might be right near the top of the list when it comes to “heartbreaking moments” by a team in the NFL.

What are the hardest to swallow though? Let's take a look back in history and try to determine the five most heartbreaking moments in Philadelphia history.

5. 2008 NFC Championship Game

We will talk about something a little later that makes this so much more heartbreaking than any normal NFC Championship game loss. And let's be honest, a loss that close to the Super Bowl is already devastating.

What also hurts, this was a close game. Philadelphia lost to the Arizona Cardinals by a final score of 32-25. They were right in it until the end.

It was the first time since 2004 that the Eagles even made it that far (again we will talk about that later). At the same time, it was the last time Philadelphia would get that far until the 2017 season, when they won the Super Bowl.

This is also significant because it was the last time the Eagles made a serious Super Bowl push with quarterback Donavan McNabb at the helm. The end of an era in Philadelphia.

4. Super Bowl XV

Now let's talk about a Super Bowl. Super Bowl XV to be exact, the first time the Eagles ever reached it to the biggest stage in professional football.

That season, saw the Eagles square off with the Oakland Raiders (now the Las Vegas Raiders). They lost that game 27-10. Sure, it wasn't the closest score, but it was 20-10 late into the contest.

What makes it hurt so bad is the fact that it was the first time Philadelphia had ever made it to the Super Bowl. So the heartbreak was a little bigger.

Then you can add onto it even more when looking back on it, because the Eagles did not find their way back to this massive game until 2004 (again, we will talk about that in a little bit).

3. Monday Night, 1997

Here is the one non-playoff moment on this list: It was a 1997 Monday Night Football game against heated rivals, the Dallas Cowboys.

This one is pretty infamous amongst Philadelphia (and probably Dallas) fans. With no time left in the game, the Eagles had a field goal opportunity. The snap was bobbled by Tommy Hutton.

Hutton then picked up the ball and tried to scramble towards the end zone. It did not end well for him though, as he was stopped short.

This wasn't just any field goal either. It was a 22-yard field goal for the win. A chip shot if there ever was one.

Instead, fans of the Eagles had to watch as Hutton failed to reach the end zone and their team lost a divisional game to one of their biggest rivals, 21-20.

2. 2001, 2002, 2003

Wow, this is rough. Philadelphia made it to the NFC Championship all three of these seasons. They lost them all.

Three straight years of reaching the NFC Championship game, and three straight losses. That really multiplies the heartbreak by quite a bit.

In 2001, the Eagles lost to the St. Louis Rams (now the Los Angeles Rams) by a final score of 29-24.

Then in 2002, the Eagles lost to the Tampa Bay Buccaneers 27-10. This was another game that was closer than it looked.

Finally, in 2003, the Eagles lost to the Carolina Panthers, 14-3.

At that point, it's impossible to think things could get much worse for Philadelphia. This stretch was just absolutely disastrous. And there's no way they could have a more heartbreaking moment, right? Right? RIGHT?!?!

1. Super Bowl XXXIX

Well let's talk about 2004 then. Once again the Eagles found themselves in the NFC Championship game. This time, against the Atlanta Falcons. And this time it was Philadelphia's turn to win the game 27-10.

So finally, that curse was broken. Philadelphia ended their three-year stretch of losing in the NFC Championship game, always so close to the Super Bowl.

Now they were actually in the Super Bowl. And things were destined to go much better for them now.

However, they met the New England Patriots in the Super Bowl. And no one that hasn't been living under a rock since 2000 needs much telling about this dynasty.

New England created one of the best dynasties of all-time. And this was just another chapter in their long story.

The Patriots won the game 24-21, with it being an absolute battle all the way through. That probably made it much more heartbreaking than if the Eagles would have just laid down and gotten smacked.

Oh, and of course, failing one game short of the Super Bowl three years in a row prior to this did not help. This was supposed to be the cleansing. This was the Eagles' redemption story, but it didn't end that way.

It was also just their second Super Bowl in franchise history, and they were still searching for their first ring at this point.

Of course, the Eagles would go on to win the Super Bowl in 2017 (against the Patriots no less). But this still has to sit as the most painful and heartbreaking moment in franchise history for most fans of Philadelphia. This was just absolutely brutal.