Historically the Philadelphia Eagles haven’t been one of the NFL’s glamour franchises. Eagles fans know pain well, having watched NFC East foes win 12 Super Bowls, including five out of six from 1990-95.
A lot of the pain has come from watching rivals win those championships and a lot of it has come from just being a bad football team for long stretches. Aside from those two aspects, quite a bit of pain came from individual games.
I will preface the list with saying that I have only been alive since 1979 so the list will be composed completely of games I personally witnessed. That is, with one large exception.
Obviously I don’t hold a monopoly on painful losses so I encourage you to share your own personal memories. It would make things even more interesting if you left a list of your own.
Without further ado, here are the 10 most painful losses in my time watching the Philadelphia Eagles.
For the record this one barely made the list. There were a few that may have deserved this spot more but as a 14-year-old it was my first Halloween without trick-or-treating.
The Eagles finished just 8-8 in 1993 as Randall Cunningham was out with an injury. Ken O’Brien was the starter in this one and just couldn’t hold up against this great Dallas team.
Everyone expected the Eagles to lose this one, but what made it so painful was how it happened. We all remember the once proud defense of the late 1980s and early 90s.
They would have never allowed Emmitt Smith to trample them for 237 yards on 30 carries. On this night the Cowboys rushed for 271 yards and two touchdowns in beating the Eagles 23-10 at the Vet.
O’Brien only mustered 107 yards through the air on 11-24 passing. It was a pitiful display and one I’ve never forgotten.
This game comes in toward the bottom for the same reason as No. 10. The Eagles weren’t expected to win this game in Dallas. What really made this one so tough was that it truly signaled the end of an era.
After 10 seasons Randall Cunningham proved completely unworthy of being the Eagles' starting quarterback.
He had lost his job to Rodney Peete of all people earlier in the season. Rodney Peete! Anyway, Randall filled in for an injured Peete and did so less than admirably.
Dallas pounded the Eagles 30-11 and it wasn’t even that close. Emmitt Smith and Michael Irvin each scored touchdowns and Deion Sanders even ran one in from 21 yards.
Adding insult to injury was the fact that a huge snow and ice storm in Philadelphia left the Eagles stranded in Dallas to stew in defeat. There was also the fact that the Cowboys went on to win their third Super Bowl in four seasons.
After losing in the opening round of the postseason the previous two seasons it was time for the Eagles to break through under Buddy Ryan.
Trailing 7-6 just before halftime, Eagles cornerback Ben Smith recovered an Ernest Byner fumble and returned it 88 yards for a touchdown. For a brief moment the Eagles led 13-7.
That was until instant replay showed that the ground caused the fumble. The Redskins kept possession and made a field goal to lead 10-6 at the half.
Randall Cunningham was pulled for a series in the third quarter, trailing just 13-6. By the time he was put back in it was 20-6 and that’s how the game ended.
The relentless Eagles pass rush was never able to sack Mark Rypien or rattle him at all. That game forced the Rich Kotite era on Philadelphia.
The Eagles lost the last two NFC Championship games and the third proved to be no different. Except for the fact that the Eagles’ offense was punchless.
They failed to score a single touchdown in the 14-3 loss. Defensive back Rickey Manning, Jr. had three interceptions in the game and manhandled receivers James Thrash, Todd Pinkston and Freddie Mitchell.
What made this even worse is this followed the miraculous 4th-and-26 game which made Eagles fans think it was a season of destiny. As it turns out, it wasn’t.
It was just another season that failed to deliver on the ultimate goal. I’ll never forget watching middle linebacker Mark Simoneau get run over by DeShaun Foster twice on the same play from the one-yard line.
Some fans would put this higher but in all honesty the Eagles were undermanned in this game. Offensive MVP Brian Westbrook and Defensive MVP Carlos Emmons were both out with injuries.
This game also led to the acquisition of Terrell Owens the following year which wasn't so bad for one season.
Prior to the 1992 season Jerome Brown lost his life in a car accident. Brown was beloved by fans and teammates alike. The team dedicated the season to his memory and vowed to bring it home for Jerome.
The season peaked in a Week 5 drubbing of the Cowboys on Monday Night Football. Philadelphia stood at 4-0 and was viewed as the league’s best team.
The Eagles were up-and-down to finish the regular season at 11-5. After an exhilarating 36-20 win over the Saints in New Orleans came a date in Dallas.
Unfortunately inspiration wasn’t enough that day. After the Eagles went up 3-0 Dallas scored the game's next 34 points. The final score was 34-10 and it was the last time Reggie White would ever wear an Eagles uniform.
This is one game that has haunted me since I was just nine. I didn’t even know a whole lot about football yet but this game truly stands alone.
Early in the game the Eagles had touchdowns called back on consecutive plays. Then on an ensuing possession tight end Keith Jackson dropped a pass in the end zone.
They settled for field goals each time. That’s eight points lost.
Then in the second quarter a thick, dense and menacing fog rolled into Soldier Field and never left. The Eagles trailed 17-9 at halftime and lost the game 20-12. Those eight points would have come in handy.
I thought this one would be higher but put it in the middle for one reason. Eagles fans love to say, “That was the year the Eagles would have won the Super Bowl!” I’ve said it many times myself.
Thinking back on it now, the Eagles weren’t competitive at all in their next two playoff games under Buddy Ryan. They were outscored by the Rams and Redskins by a combined 41-13.
The Eagles weren’t good enough to get through the 49ers so this one feels less painful now than it did on New Year’s Eve all those years ago.
This is the one exception to my rule of games I personally witnessed. I was still shy of two years old at the time.
Regardless of whether I watched or remember this game it’s the Super Bowl!
Dick Vermeil and Ron Jaworski were running like a well-oiled machine in 1980. They had just destroyed the Cowboys in the NFC Championship game and the Phillies had won their first World Series just a few months before.
Everything was lined up perfectly for Philadelphia sports until the Oakland Raiders pillaged and plundered the hopes of Philadelphia.
Jaws was intercepted by Rod Martin three times in the game and Jim Plunkett through three touchdown passes for the Raiders.
The Eagles wouldn’t return to the Super Bowl for almost 25 years.
The 2008 season was a weird one. The Eagles completely fell apart, falling to 5-5-1 after a 36-7 beating at the hands of the Baltimore Ravens.
After dropping a game to the Redskins all hope was lost. That is until three days after Christmas.
The lowly Raiders knocked off the Tampa Bay Buccaneers in the early game to set up a showdown between the Eagles and Cowboys for the final playoff spot.
The Eagles massacred Dallas 44-6 to get into the tournament. They responded by winning in Minnesota and eliminating the defending Super Bowl champion New York Giants. All that was left was a game in Arizona.
The Eagles fell behind 24-6 at the half. Donovan McNabb led a furious rally to take a 25-24 lead early in the fourth quarter.
Unfortunately Kurt Warner got the ball one more time and led a 14-play, 72-yard touchdown drive that ran 7:52 off the clock. Similar to the 2001 NFC title game, McNabb didn’t have enough bullets left to bring the Birds back.
They ultimately lost 32-25 with David Akers having missed a field goal, an extra point and cost the team three points with a kickoff that went out of bounds.
It was the last time Brian Dawkins or Jim Johnson would have their fingerprints on an Eagles game. It was the official end of a great era.
Brady didn't get the Eagles' best shot in Super Bowl XXXIX.
Honestly, when this game ended it didn’t really hurt. The feeling was just complete numbness. For the first time ever I had just watched a Super Bowl with the Eagles actually playing in it.
They had some great moments. They had New England on the ropes. T.O. was truly heroic. The Eagles didn’t get outplayed really. They beat themselves with mistakes early.
If only Donovan could have avoided the interception in the red zone. If only L.J. Smith could have just gone down instead of fumbling. If only they could have scored before the two-minute warning.
The thing is, Donovan did throw that pick. L.J. did fumble the ball. The Eagles did score too late to have a chance to win on the final possession.
The Eagles were never the same after that defeat. They were the elite NFC team for four years and quickly devolved into a soap opera.
There was the T.O./McNabb spat. Then there was T.O. being sent home from camp and doing sit ups in his driveway. There was the release of T.O. and the troubles of Andy Reid’s sons. There is so much more as well.
This game didn’t just mean the Eagles wouldn’t win Super Bowl XXXIX, it marked the end of the Eagles as we knew them.
I don’t even know how to properly describe this one. I was in my third year of season tickets. It was the last Eagles game at the Vet. It was the Buccaneers, who the Eagles had owned.
It was the perfect setup for a Super Bowl season. The Eagles started with a bang as Brain Mitchell took a kickoff deep into Tampa territory. It was quickly followed by an incredible Duce Staley touchdown run.
The Vet had never been more alive. Then the offense stalled. Then Blaine Bishop, who stayed in the game despite a torn groin helped to allow a 71-yard catch-and-run by Joe Jurevicius to set up Tampa’s first touchdown.
He was also beaten on their second touchdown by Keyshawn Johnson.
The Eagles trailed 20-10 with over three minutes to play. They drove to the Tampa Bay 10-yard line. A touchdown would make it a three-point game with plenty of time on the clock.
Only McNabb dropped back and fired and Ronde Barber made the interception and ran it 92 yards for a touchdown. The Buccaneers would go on to win 27-10.
I can still see Barber running almost 10 years later. The Bucs would go on to crush the Raiders in the Super Bowl. Now that was the year the Eagles would have won it all. Except they didn’t and they still haven’t.