Most Heartbreaking Moments in World Football History

The thrill of victory for one side is always balanced by the agony of defeat for another leaving one set of players crumbled on the pitch while their opponents celebrate wildly.

Inevitably, some losses are much more painful than others. Whether it is the circumstances that decide the match or the magnitude of the contest itself, tear-jerking losses come in many different forms.

Here are some of the most heartbreaking losses in world football history in no particular order.

Which of these losses was the most difficult to swallow? Let us know what you think by leaving your comments below.

Note: Football has had its fair share of tragedy with the Hillsborough disaster and too many others unfortunately coming to mind. You can also add in the tragic loss of various players who have passed away as a result of heart-related complications on the pitch.

While they are not featured on this list—as it focuses solely on match results—the victims of these events should never be forgotten.

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AC Milan vs. Liverpool: 2005 Champions League Final

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When Liverpool fell behind AC Milan 3-0 before the halftime whistle had even sounded it seemed like the 2005 Champions League crown was well out of reach.

Two goals from Argentine Hernan Crespo were preceded by a surprising strike from legendary defender Paolo Maldini which had Milan heading into the locker room with the victory all but secured.

Even the most passionate, optimistic Liverpool supporters certainly thought Ol’ Big Ears would be heading to Italy.

And we all know what happens now, right?

Steven Gerrard, Vladimir Smicer and Xabi Alonso provided the goals for one of the most thrilling comebacks in football history. The crowd at the Ataturk Stadium in Istanbul was in utter shock; the Liverpool fans were boisterous while the Milan supporters were silent.

Liverpool would go on to lift the trophy after Jerzy Dudek backstopped his club to a famous 3-2 victory in the penalty shootout.

USA vs. Japan: 2011 Women’s World Cup Final

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With the nation attempting to recover from a devastating tsunami and subsequent nuclear disaster, Japan was given a boost by its women’s soccer team breaking American hearts in the process.

The U.S. managed to take the lead on two separate occasions with strikers Alex Morgan and Abby Wambach giving the heavily favored Americans a 1-0 and then 2-1 lead.

But Japanese star Homare Sawa ensured that the match would go to penalties as the captain netted a goal in the 117th minute to keep Japanese hopes alive once again. The tying goal to send the match to extra time was scored late as well in the 81st minute of the thrilling match.

With all of the momentum now in its corner, Japan would go on to win the World Cup on penalties as goalkeeper Ayumi Kaihori stopped three American shooters to give her nation its biggest win in soccer history.

Chelsea vs. Barcelona: 2009 Champions League Semifinal

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Barcelona managed to break Chelsea hearts in 2009 after one of the more controversial matches in Champions League history.

The match is often remembered for the curious refereeing display by Norwegian official Tom Henning Ovrebo who denied Chelsea two clear penalties with fans of the Blues suggesting there could have been a couple more as well.

The English side led the match 1-0 following a thunderbolt first-half goal from midfielder Michael Essien (which also gave them a 1-0 lead on aggregate) so things looked good for the Londoners despite their displeasure with Ovrebo.

That is when Andres Iniesta scored in the 93rd minute to snatch a place in the Champions League final and send Chelsea home disappointed once again following their loss to Manchester United in the final of the competition the previous year.

Ghana vs. Uruguay: 2010 World Cup Quarterfinal

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In the first World Cup ever played on African soil, Ghana made it to the quarterfinals of the tournament with an opportunity to make a groundbreaking appearance in the semifinal which would have been the first ever for an African nation.

The only thing standing in the way for the Black Stars was Uruguay.

After an enthralling back-and-forth encounter that saw the match tied at one late in extra time, Ghana was given the chance to make history.

After Ghana striker Dominic Adiyiah headed the ball beyond Uruguayan keeper Fernando Muslera, Luis Suarez raised both hands to ensure that the ball didn’t cross the line. Suarez was given a red card and Ghana was awarded with the potential winning penalty kick.

When Asamoah Gyan—the team’s leading scorer and talisman at the tournament—stepped up to the spot, the storybook ending was already being written around the world.

That was until Gyan blasted his kick off the crossbar giving Uruguay a lifeline it would not pass up.

The South Americans would go on to win the match 4-2 on penalties breaking not only Ghanaian hearts but those of the entire continent.

Arsenal vs. Manchester United: 1979 FA Cup Final

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In a match that has been dubbed the “five-minute final”, Arsenal found itself up 2-0 against Manchester United with the aforementioned amount of time remaining on the clock.

The fans at Wembley Stadium were then treated to a thrilling conclusion as two goals in a two minute span from Gordon McQueen and Sammy McIlroy put the Red Devils on level terms.

All signs pointed towards United going ahead and winning the match as Arsenal supporters in the crowd were stunned at what they had seen.

But the emotional roller coaster finished on a high note for the Gunners as Alan Sunderland slid in at the back post to turn Graham Rix’s cross into a goal just a minute later meaning Manchester United’s incredible effort was all for naught.

Italy vs. France: 2000 European Championship Final

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Two years after it captured the World Cup title, France added the 2000 European Championship to its football repertoire. To do so, the French crushed Italian hopes with a thrilling 2-1 comeback victory.

With the Azzurri leading 1-0 thanks to a 54th minute goal courtesy of striker Marco Delvecchio—who was a surprise inclusion in the starting eleven, replacing Filippo Inzaghi—the match moved into the final minutes, and the Italian players stood on the sidelines ready to rush onto the pitch in celebration.

That was until former Arsenal man Sylvain Wiltord broke their hearts with a goal in the 93rd minute firing a low drive beyond goalkeeper Francesco Toldo to send the contest into extra time.

Buoyed by the equalizer, France would go on to claim the Henri Delaunay Trophy when David Trezeguet smashed a fabulous first time volley into the roof of the net after 103 minutes giving Le Bleus a famous victory.

Italy would get its revenge in 2006, but this loss to France still hurts for many fans of the Azzurri.

Turkey: 2008 European Championship Journey

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Turkey’s journey at the 2008 European Championship in Austria and Switzerland was heartbreaking for almost everybody they crossed.

Last minute goals defined the tournament for the Turks who progressed out of the opening group stage thanks to a 92nd minute goal by Arda Turan against Switzerland as well as an 89th minute winner by Nihat Kahveci in the final group match against the Czech Republic which secured a thrilling 3-2 comeback victory.

But they weren’t done there.

Turkey met Croatia in the quarterfinal where Ivan Klasnic put the Croatians ahead in the final minute of extra time and looked to have ended Turkey’s run. But incredibly, the comeback kings of the tournament lived up to their billing as Semih Senturk struck in the 123rd minute which sent the match to penalties.

Turkey would progress to the semifinal with a 3-1 victory in the penalty shootout before ironically being eliminated by Germany courtesy of a last minute winner from defender Philipp Lahm.

Bayern Munich and Schalke: 2000-01 Bundesliga Conclusion

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One of the more heartbreaking moments on this list came after a team actually won its match.

The final day of the 2000-01 Bundesliga campaign saw perennial power Bayer Munich atop the table once again leading Schalke by three points when they travelled to Hamburg needing just a draw to claim the title due to an inferior goal difference.

With Schalke claiming a 5-3 victory at home over SpVgg Unterhaching, they needed news of a goal from Hamburg in order to get their hands on the league trophy.

They got it from Bosnian midfielder Sergej Barbarez when he struck in the 90th minute to give Hamburg a 1-0 lead. When news broke of the goal, Schalke fans rushed the pitch in celebration of what they assumed would be a league championship.

But in the third minute of injury time as Schalke supporters continued to rejoice, Bayern Munich defender Patrik Andersson netted the equalizer that gave the Bavarian giants the point they needed to secure the 17th league title in club history.

As Bayern fans reveled in the result, Schalke’s joy instantly turned to shock.

Celtic and Rangers: 2004-05 Scottish Premier League Conclusion

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The Scottish Premier League is too often derided for being a two horse race that doesn’t offer much variety from year to year.

But that certainly hasn’t taken away from the magic and excitement the league has conjured up in recent years with the title often coming down to the final day of the campaign.

On the final day of the 2004-05 Scottish Premier League season, bitter rivals Celtic and Rangers once again found themselves fighting for the title.

Celtic travelled to Fir Park for a meeting with Motherwell on the last match day of the campaign while Rangers simultaneously took on Hibernian at Easter Road to decide who would claim the league crown.

With both clubs leading their respective matches 1-0 and time ticking away, Celtic was poised to claim the title.

That was until Motherwell striker Scott McDonald equalized with a goal in the 88th minute before scoring again within three minutes to secure a 2-1 victory for the home side.

That result, coupled with Rangers’ ability to hold on and capture three points meant that The Gers finished the season one point ahead of their hated adversaries.

Italy vs. Germany: 2006 World Cup Semifinal

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Another match where injury time steals the show.

European rivals Italy and Germany played an enthralling 118 minutes of scoreless football in front of 65,000 fans in Dortmund before the pro-German crowd had its heart broken.

After left back hero Fabio Grosso scored one of the more memorable goals in World Cup history—followed by one of the more emotional celebrations—cameras showed utter despair in the crowd as fans with German flags and face paint were reduced to tears.

Juventus legend Alessandro Del Piero would secure the result with the final kick of the match minutes later as Italy stopped Germany from making an appearance in the showpiece event of the tournament in Berlin.

Manchester United vs. Bayern Munich: 1999 Champions League Final

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“Football, bloody hell.”

That’s how legendary Manchester United manager Sir Alex Ferguson described this match immediately following the final whistle.

Going into the contest, the English giants had already secured the Premier League title and FA Cup. Only Bayern Munich was standing between them and a historic treble.

Without influential midfielders Roy Keane and Paul Scholes, the task was made even more difficult after Mario Basler swept in a low, curling free kick beyond Peter Schmeichel in only the sixth minute of the match to give the Bavarian club a dream start.

After the two clubs exchanged chances throughout the match, Bayern looked destined for the victory as the clock ticked beyond the 90-minute mark with the score remaining 1-0.

That was until super-subs Teddy Sheringham and Ole Gunnar Solskjaer stunned over 90,000 fans on hand at the Camp Nou by scoring a goal each in injury time—both stemming from David Beckham corners—to snatch the trophy from the Germans.

Manchester United didn’t get the reputation for its fighting spirit and never-say-die attitude by mistake.

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