Top 10 Most Heartbreaking Losses in Philadelphia Sports History

Being a Philadelphia sports fan is rough. You get your hopes up at the beginning of each year only to wind up feeling devastated by the end of it. Here are 10 of the most heartbreaking losses in Philadelphia sports history.

The Top Ten

1 Eagles - 2002 NFC Championship Game vs. Tampa Bay Buccaneers The Philadelphia Eagles are a professional football franchise based in Philadelphia, Pennsylvania. The Eagles compete in the National Football League as a member club of the league's National Football Conference East division.

Everything seemed to be set up perfectly for the 2002 Philadelphia Eagles in a poetic fashion. They had a fantastic 12-4 regular season despite young star QB Donovan McNabb being out for six games, and Andy Reid ended up winning Coach of the Year. Their defense was absolutely stacked and was led by the late great Jim Johnson. Heading into the 2002 NFC Championship Game against the Tampa Bay Buccaneers, there was not much reason to be nervous. Despite their historically ferocious defense, Tampa had a limited offensive attack and notoriously struggled in colder weather. Not only that, but the Eagles had destroyed them in their previous two playoff matchups in 2001 and 2000, as well. It would be the final Eagles game ever played in Veterans Stadium, and the Birds seemed destined to end their tenure with a triumph. When veteran kick returner Brian Mitchell returned the opening kickoff deep into Tampa territory, everything seemed to be falling into inevitable place. But the Eagles ended up ...more

2 Phillies - The 1964 Collapse The Philadelphia Phillies are an American professional baseball team based in Philadelphia, Pennsylvania. The Phillies compete in Major League Baseball as a member club of the National League East division. They play their home games at Citizens Bank Park. They won the World Series in 1980 and 2008.

I love the Phillies. I will always love the Phillies. I will be a fan of theirs until the day I die. But let's be honest here. Historically as a franchise, they have been complete losers. They have been around ever since the World Series was invented in 1903, and they have only won 2 titles. The Marlins have been around for 26 seasons, have only made the playoffs twice, and they have as many World Series rings as the Phillies. They lead all of professional sports with the most total losses, losing more than 10,000 games in their history. Out of all the franchise's failures, the most notorious will always be their collapse in the 1964 season, known as the "Phold of '64" - a moment that will live in the zeitgeist of Philadelphia sports fandom forever. The club had a 6 1/2 game division lead with 12 games left to play in the regular season, and a National League pennant seemed certain. However, an unpredictable ten game losing streak occurred in September as the Phillies ended up ...more

3 Phillies - 1993 World Series Game 6 vs. Toronto Blue Jays The Philadelphia Phillies are an American professional baseball team based in Philadelphia, Pennsylvania. The Phillies compete in Major League Baseball as a member club of the National League East division. They play their home games at Citizens Bank Park. They won the World Series in 1980 and 2008.

You know how the 2019 Phillies were supposed to blossom into a World Series contender only to once again succumb to the mediocrity that the franchise has been marinating in for the better part of a decade? Well, the exact opposite happened for the 1993 version of the team. Nobody expected this team to be good. They weren't even good after this year and wouldn't make the playoffs again for another 14 years. But in one of the most bizarre and unpredictable one-year-wonders in the history of sports, the Phillies absolutely ruled the baseball world in 1993. Their gritty play and unexplained winning with a rag-tag group of likable personalities that included Lenny Dykstra, John Kruk, Darren Daulton, Curt Schilling, Dave Hollins, and Mitch "Wild Thing" Williams captured the city's imagination. It almost seemed like a group of drunken community softball players had gotten together and put on the red pinstripes, but they were somehow inexplicably really, REALLY good. After a huge upset over ...more

4 76ers - 2019 Eastern Conference Semifinals Game 7 vs. Toronto Raptors The Philadelphia 76ers are an American professional basketball team based in the Philadelphia metropolitan area.

Even though we are only one year removed from this game at the time I am writing this, the 2019 76ers season seems like a lifetime ago. Integral pieces such as Jimmy Butler, JJ Redick, and TJ McConnell have moved on as the team is currently floundering and trying to refind and reestablish an identity. Much of that is due to the overwhelming incompetence of head coach Brett Brown and the beyond questionable knee-jerk decision-making of GM Elton Brand but I digress. We're talking about one series and one play that elevated a young but frustrating franchise into championship glory while sinking another franchise into deep pits of despair. While the Sixers certainly appeared to be more talented than the Raptors on paper, Toronto had several key advantages. One: They had played a full season together and were fully used to playing with one another while the Sixers played with three versions of the same team in one season. Two: Even with Joel Embiid limited with injuries and sickness, the ...more

That one must of hurt.

5 Flyers - 2000 Eastern Conference Finals Game 7 vs. New Jersey Devils The Philadelphia Flyers are a professional ice hockey team based in Philadelphia. They are members of the Metropolitan Division of the Eastern Conference of the National Hockey League.

The Flyers were at a bit of a crossroads coming into the new millennium. They had a very talented roster but appeared to have already peaked in terms of reaching their full potential as a team. They had reached the Stanley Cup Finals in 1997 only to be swept by a burgeoning empire in the Detroit Red Wings. Polarizing superstar forward Eric Lindros had been stripped of his captaincy by president and GM Bob Clarke, and would not play at the beginning of the 2000 Stanley Cup playoffs. Despite Lindros' absence, the Flyers galvanized themselves in the postseason and went on a run that led them to the Eastern Conference Finals against a very tough and defense-oriented New Jersey Devils team. Up 3-1 in the series, the Flyers appeared to be on their back way to the Cup Finals only to lose the next two games. However, Lindros had returned for Game 6, and Game 7 would be on Philadelphia home ice. The cards seemed to be aligned for a Flyers victory. Then Scott Stevens did what Scott Stevens ...more

6 Flyers - 2010 Stanley Cup Finals Game 6 vs. Chicago Blackhawks The Philadelphia Flyers are a professional ice hockey team based in Philadelphia. They are members of the Metropolitan Division of the Eastern Conference of the National Hockey League.

Much like the 1993 Phillies, the 2010 Flyers appeared to be a team of destiny. They had to win in a shootout against the Rangers in the last game of the season in order to make the playoffs, and once they were in, they went on one of the most exciting playoff runs in NHL history. They upset the 2-seeded Devils in the first round, came back from a 3-0 series deficit against the Bruins in the second round by erasing a 3-0 lead in Game 7, and they dispatched a red-hot Canadiens team that was on their own magical ride in the East Finals. The only team that remained was a young and hungry Blackhawks squad that was looking to deliver the franchise's first Stanley Cup since 1961. After a rough handful of games that involved stellar goals, poor goaltending, big hits, bad blood, and puck stealing, the Flyers found themselves in overtime of Game 6 down in the series 3 games to 2, needing to score to push the series to a Game 7. However, any hope of winning the city's first Cup since 1975 ...more

7 Phillies - 2011 NLDS Game 5 vs. St. Louis Cardinals The Philadelphia Phillies are an American professional baseball team based in Philadelphia, Pennsylvania. The Phillies compete in Major League Baseball as a member club of the National League East division. They play their home games at Citizens Bank Park. They won the World Series in 1980 and 2008.

I consider myself very lucky that I was able to grow up during arguably the greatest era in Phillies' franchise history. The Phillies won the NL East five years in a row from 2007 to 2011 and won a World Series in 2008. Featuring iconic players such as Jimmy Rollins, Chase Utley, Ryan Howard, Cole Hamels, Roy Halladay, Shane Victorino, Carlos Ruiz, Jayson Werth, and Brad Lidge, these teams endeared themselves to Philadelphia with their winning ways and swagger. The Phillies had just completed a phenomenal season winning 102 games, the best total in all of baseball. They were heavy World Series favorites and just needed to get past a scrappy and resilient Cardinals team to continue their run towards further October glory. In the deciding Game 5 at Citizens Bank Park, the Phillies usually stellar bats went uncharacteristically cold at the worst time. Usually a variety of factors come into play that causes a juggernaut to fall from grace. But in this case, the death of this Phillies team ...more

8 Eagles - 2008 NFC Championship Game vs. Arizona Cardinals The Philadelphia Eagles are a professional football franchise based in Philadelphia, Pennsylvania. The Eagles compete in the National Football League as a member club of the league's National Football Conference East division.

I'm not sure where this game would normally rank amongst Philadelphia sports fans, but this was truly my first experience of firsthand heartbreak as a Philadelphia sports fans. I'm biased in this situation. I was 10 years old when this game was played and I will always remember it as the first time a professional sporting event made me feel truly sick to my stomach. The Eagles had sneaked into the playoffs with a record of 9-6-1 after destroying the Cowboys in the final game of the regular season. They were up against a similarly underwhelming 9-7 playoff team in the Cardinals in the NFC Championship. I remember for some reason being at a bowling alley during the game for whatever reason, and I also remember Larry Fitzgerald absolutely torching the Eagles defense in ways that I did not believe were humanly possible. The Eagles lost the game and the game would be the fourth NFC Championship that the Eagles would lose during the Andy Reid era. While the Eagles would have had a very ...more

9 Eagles - Super Bowl XXXIX vs. New England Patriots The Philadelphia Eagles are a professional football franchise based in Philadelphia, Pennsylvania. The Eagles compete in the National Football League as a member club of the league's National Football Conference East division.

Whenever you make the Super Bowl, you need to operate under the assumption that you will never make it there again, and you need to make every moment and opportunity count once you are there. After losing three straight NFC Championship Games from 2001 to 2003, the Eagles finally punched their ticket to the big one under Andy Reid in 2004. The only problem was that they had to play a juggernaut in the New England Patriots who had won 2 of the previous 3 Lombardi Trophies. The Eagles fought valiantly against New England and Terrell Owens pulled out an incredibly gutsy performance with a broken leg, but at the end of the day, the Patriots were just too much for the Eagles. The game was an absolute heartbreak for Eagles fans who had to watch their team lose in the big game after watching them just miss out on the game in the previous three seasons. Coincidentally, this game is probably one of the least talked-about Super Bowls of all time in my opinion. If the only highlight that people ...more

10 76ers - 1981 Eastern Conference Finals Game 7 vs. Boston Celtics The Philadelphia 76ers are an American professional basketball team based in the Philadelphia metropolitan area.

A lot of people mention how the late 2000s-early 2010s Phillies are a team that should have won more championships than they did given the talent that was on their roster. I believe that the Julius Erving-era 76ers are an even more blatant example of this. The 1983 team is a legendary, probably Top 15 team in NBA history, but the team had many more chances to win it all before Moses Malone was the new kid in town. They should have probably beaten the Trail Blazers in the 1977 Finals, they should have had a better time in the 1980 Finals with Kareem Abdul-Jabbar missing time due to injury, and they should have finished off the Celtics when they had the chance in the 1981 Eastern Conference Finals. Up 3 games to 1 in the series, the Sixers blew their chance to reach another Finals and a potential matchup against a substantially weaker Houston Rockets squad that finished with a losing record in the regular season. This was just a major blown opportunity for the Sixers to win it all. It ...more

The Contenders

11 Eagles - Super Bowl XV vs. Oakland Raiders
BAdd New Item