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The 50 most heartbreaking moments in football

Paul Gascoigne, most heartbreaking moments in football
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Every football fan is well versed in just how thin the line can be between joy and despair. 

But in the long, complex history of the sport, some clubs and national teams have been made to suffer more than others. 

In the following list, we run through 50 of the most heartbreaking moments to take place on a football pitch. 

This list is for moments of football-related heartbreak like cruel results, controversies and career lows, and not examples of tragedy or horror around the game.   

Read on, and try not to wince...

1950: Uruguay break Brazilian hearts

The final match of the 1950 World Cup was supposed to be a procession. Brazil’s newspapers had already printed special editions describing the Selecao as ‘Champions of the World’ before kick-off, and 200,000 fans packed into the new Maracana Stadium expecting to witness history being made against underdogs Uruguay. 

However, disaster struck as the Uruguayans came from behind to win 2-1 and clinch their second World Cup title, leaving the enormous crowd in tears in what has gone down as one of Brazilian football’s darkest days.

1974: Total Football meets its match

The world fell in love with a Johan Cruyff-inspired Netherlands team as they marched to the 1974 World Cup final with their groundbreaking ‘Total Football’ style in its pomp.

Coach Rinus Michels won hearts and minds with an aggressive and skilful team that took down Argentina and Brazil, but they fell to West Germany in the Munich final in what was undoubtedly their best-ever shot at becoming world champions. 

1975: Leeds feel robbed in European Cup final

Leeds 1975

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Leeds (opens in new tab) travelled to Paris for the 1975 European Cup final against Bayern Munich (opens in new tab)hoping for the crowning moment of a glorious era, but things soon turned sour as they were denied a stonewall penalty and had a goal disallowed before losing to two goals in the final 20 minutes.

It was all too much for Whites fans in the stadium, who raged at the perceived injustice by ripping up seats and causing damage in the city. Leeds haven’t made it so far in Europe since.    

1979: United’s cup final comeback cut short

Manchester United (opens in new tab) fans have enjoyed more than their fair share of success over the years, but they were left crestfallen back in 1979 after arguably the most thrilling conclusion ever to an FA Cup final. 

Arsenal (opens in new tab)were cruising at 2-0 up as the seconds counted down to full-time, but United mounted  superb comeback by striking on the 87th and 88th minutes – only to then concede an 89th minute Gunners winner. Ouch. 

 

1982: El Salvador suffer worst-ever World Cup defeat

In their first World Cup in 1974, El Salvador lost three games, conceding nine goals and scoring none.

In their very next World Cup game, they did at least score. But the 10 goals Hungary put past them mean that Luis Ramires Zapata's goal remained a fairly underwhelming consolation.

1990: Gazza’s tears

Paul Gascoigne

(Image credit: Getty)

Oh, Gazza. The wobble of the England midfielder’s bottom lip after he received a yellow card that would have ruled him out of the 1990 World Cup final softened even the hardest of hearts. 

The Three Lions never made it there, going on to lose on penalties to West Germany, but it was the moment a nation fell in love with the precociously talented youngster.

1993: Nottingham Forest relegated in Clough's final season

"I'm a happy man," protested a tearful Brian Clough on the day Forest were relegated from the Premier League. "Happiness comes from the inside. I'm a good socialist, I'm a good dad, I'm a good grandad. I'm happy."

Cloughie had turned Nottingham Forest from Second Division strugglers into back-to-back European champions, but retired from the game in a manner no one wanted to see: they finished rock-bottom of the Premier League's inaugural season, and seeing one of the greatest managers ever almost moved to tears was tough.

1994: Baggio's penalty heartache

Roberto Baggio’s crucial penalty miss in the final of the 1994 World Cup is up there with the cruellest moments in football history. 

The Divine Ponytail inspired the Azzurri’s run to the showcase game, and he remains one of the finest footballers his country has ever produced, but his moment of weakness from 12 yards would haunt him for the rest of his career. 

1996: Newcastle 'Entertainers' blow title shot

Newcastle (opens in new tab)looked destined to become English champions for the first time since 1927 when Kevin Keegan’s ‘Entertainers’ stormed 12 points clear at the top of the Premier League table in January 1996, with 15 games to go.  

But their subsequent dive in form allowed Manchester United to catch up and by the final day Newcastle needed to beat Spurs and hope for a United defeat against Middlesbrough. Spurs claimed a draw, Alex Ferguson’s side won 3-0, and the collapse was complete. 

1996: Scots one goal short of Euro knockouts

Scotland Euro 96

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Scotland have never made it to the knockout stages of a major tournament, but their exit from Euro 96, held in neighbouring England, was particularly painful.

After a draw and a defeat, Scotland needed to beat Switzerland and hope for the Dutch to lose by four goals or more to England in the final round of group games.

The dream was on as the Scots led the Swiss 1-0 and England were 4-0 up against Holland, but Patrick Kluivert’s 78th-minute consolation proved crucial. The two sides finished level on points and goal difference, but the Oranje progressed on goals scored. Urgh.

1996: Southgate penalty miss ends England's run

England’s Euro 96 run on home turf raised hopes once more, six years on from reaching the final four at the World Cup, that a major tournament win could be in the offing, only to come undone on penalties (again) against the Germans (again) in the semi-finals (again).  

Southgate’s effort was saved in sudden death, and he has since spoken openly about how much it affected him at the time and ever since. At least he’s since become a national treasure as England manager.

1998: Gazza doesn't make the World Cup cut

Paul Gascoigne's career is littered with heartbreak and ideas of what could have been: never the same after his leg break in 1991, off-pitch problems also played their role in Gazza failing to reach his potential.

Being left out of Glenn Hoddle's England squad for France 98 bookended his career with another moment of sadness. At 31, he could have been the only player who appeared at Italia 90 to make the team, but it wasn't to be.

1998: Beckham sees red 

A flick of the right leg was enough to turn David Beckham from hero to villain at France ’98, as the midfielder’s reaction to a Diego Simeone challenge was enough to earn him a red card. 

Early in the second half, with the last 16 tie level at 2-2, Becks was sent off. England still managed to take the game to penalties, where (of course) they lost, but the reaction of the press and public was unforgiving as the Manchester United man was blamed for his country’s elimination.

1999: Batistuta injury ends Fiorentina's title surge

In February 1999, Fiorentina and their star man Gabriel Batistuta were flying high, with the Florence club top of the league and their Argentinian striker top scorer in Serie A.

But a 0-0 draw with AC Milan derailed everything, as Batistuta was carted off injured and ruled out for more than a month. La Viola’s form dived without him, and they ultimately finished third, with one of their greatest players unable to lead them to title.  

2000: Injury problems begin for Ronaldo 

Ronaldo Inter

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There was no stopping ‘O Fenomeno’ in the late ‘90s, with the Ballon d’Or and World Cup-winning striker scoring at a formidable rate until he faced career-threatening injury issues. 

The Brazilian returned from a ruptured knee tendon to feature for Inter Milan against Lazio in the Coppa Italia final, but lasted just six minutes before rupturing the tendons in his knee cap, in what would become a recurring issue for the rest of his career.

2001: Schalke title celebrations cut short

For a few minutes, Schalke thought they were Bundesliga champions. Going into the final day of the 2000/01 season, the German side were three points behind Bayern Munich, but they had a better goal difference.

After being Unterhaching 5-3, word spread that Hamburg had beaten Bayern 1-0 and celebrations of a first Schalke title since 1958 began. But they were premature, as Bayern scored a 94th-minute equaliser to pinch the title from under their noses in the most painful way imaginable.

2002: Leverkusen's horror treble

Rarely has hope turned to ash quite as spectacularly as it did for Bayer Leverkusen at the end of the 2001/02 season.

The Germans were on course for a remarkable treble as the season run-in arrived: top of the Bundesliga, and in the finals of the Champions League and DFB-Pokal.

But they somehow blew a five-point league lead in a week to finish second behind Borussia Dortmund, before losing the cup final 4-2 to Schalke and falling to Real Madrid at Hampden Park in the European decider. 

2002: Ireland pay the penalty

Ireland were agonisingly close to taking a major scalp at the 2002 World Cup, but penalties proved to be their undoing. 

Fernando Morientes put Spain ahead early on before Ian Harte missed a spot kick, but Robbie Keane equalised in the last minute. The Irish had chances to win it in extra-time but couldn’t take them, and a shoot-out defeat was a sad and undeserved end to their run.

2003: Balde sees red in UEFA Cup final

Bobo Balde

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Celtic (opens in new tab) took down Blackburn, Celta Vigo, Stuttgart, Liverpool and Boavista on their thrilling run to the 2003 UEFA Cup final, but they suffered an agonising extra-time defeat in the final to Jose Mourinho’s Porto.

Henrik Larsson twice drew the Bhoys level to send the game to extra-time, but Bobo Balde earned a second yellow and his team couldn’t hold out with ten men as Derlei scored his second of the night with five minutes to go. 

The big defender, who had played such a big part in getting his team that far, was left distraught. 

2005: Collina denies Dunc

Pierluigi Collina was responsible for one of the more painful ‘what if’ moments for Everton (opens in new tab)fans, as the legendary Italian referee controversially ruled out a towering Duncan Ferguson header in their Champions League qualifier at Villarreal.

If the goal had stood, it would’ve drawn the tie level at 3-3 and beckoned extra-time. But the Spaniards went on to win 4-2 on aggregate, and the Toffees’ still haven’t returned to Europe’s top competition since 1970-71. 

2006: Zidane loses his head

Zinedine Zidane

(Image credit: PA)

The stage was set for Zinedine Zidane, arguably the finest player of his generation, to bow out in the most glorious way imaginable 

The final game of the playmaker's career was the World Cup final, and his Panenka penalty put Les Bleus ahead after just seven minutes. 

But things unravelled when Marco Materazzi, who had earlier equalised for Italy, said something to Zidane in extra-time that made the great No.10 turn around and slam his balding head into the defender’s chest. France went on to lose on penalties – with Materazzi among the Azzurri’s scorers.

2006: Lasagna-gate

On the final day of the 2005/06 season, Spurs (opens in new tab)faced West Ham needing to match Arsenal’s result against Wigan to qualify for the Champions League, and therefore reach Europe’s top competition for the first time since 1961/62.

But a mass outbreak of illness left 10 players out of action. Spurs lost, Arsenal won, and conspiracy theories abound about possible food poisoning at the team hotel, although the Health Protection Agency later said there were no signs of that being the case.

2006: Lehmann makes unwanted history

Former Arsenal (opens in new tab)goalkeeper Lehmann holds the unwanted record of being the first player to be sent off in a European Cup final, after he saw red 18 minutes into their 2-1 defeat to Barcelona.  

The German rushed to the edge of his box and wiped out Samuel Eto’o before Ludovic Giuly stuck the loose ball into an unguarded net, but the referee didn’t allow the advantage to be played and instead came back to the foul to send off the keeper. 

Would things have turned out differently if the goal had stood and the game continued 11 v 11? We’ll never know.

2007: Baggies fall to record-setting Rams

West Brom (opens in new tab) dominated the 2007 Championship play-off final but couldn’t find a way past Derby goalkeeper Stephen Bywater, and the Rams eventually won 1-0 through a Stephen Pearson strike.

It wasn’t just the manner of the defeat that was painful for the Baggies, but the fact that their conquerors went on to become the worst team in Premier League history the following season, registering just 11 points. 

2009: Le Hand of God

Oh VAR, where art thou? If the on-field review system was in place back in 2009, Ireland may well have ended up at the World Cup in South Africa at the expense of reigning world champions France.

Instead, Thierry Henry got away with a blatant handball to set up William Gallas’ goal in a 2-1 aggregate play-off victory for Les Bleus. The injustice of it all still rankles.

2009: Iniesta sinks Chelsea

Barcelona made the most of their only shot on target against Chelsea (opens in new tab)in the Champions League semi-final second leg in London, as Andres Iniesta pinged one into the top corner first time in the dying seconds of a thrilling tie to win it on away goals.   

The Blues were furious, after having several penalty claims turned down, leading to an angry Didier Drogba’s famous shout down the camera lens at full-time: “It’s a f**king disgrace”.

2009: Duff own goal sends Shearer-led Newcastle down

Newcastle’s (opens in new tab)relegation from the Premier League was a painful time for the Toon Army, but the way it was confirmed made it even more so.

Damien Duff deflected a Gareth Barry strike into his own net to seal a 1-0 defeat to Aston Villa that ended the Magpies’ 16-year stay in the top flight. The fact that Tyneside legend Alan Shearer had been drafted into the dugout to try and help turn the tide made the slide all the more bitter.

2010: Forlan finishes Fulham fairytale

Fulham (opens in new tab)won over neutrals during their surprise run to the 2010 Europa League final, but they were undone by Atletico Madrid with a penalty shoot-out just four minutes away.

Diego Forlan, who scored the opener before Simon Davies equalised in the first half, beat Mark Schwarzer with a deflected effort late on as the Cottagers suffered defeat in their first major final appearance since the 1975 FA Cup…which they also lost.

2010: Lampard’s ghost goal

Listen up, kids. In days gone by, referees didn't have a watch on their wrist to let them know if the ball crosses the line.

The thing that made Frank Lampard’s ‘ghost goal’ against Germany at the 2010 World Cup particularly painful was: a) it was a screamer that would’ve drawn England level and b) it was obvious to pretty much everyone in the world apart from the referee that it went in.

2010: Suarez swats Ghana out of World Cup

Luis Suarez is often the pantomime villain, but arguably never more so than when he shithoused Ghana out of the World Cup. 

The Black Stars, looking to become the first African side to reach the semi-finals, were denied an extra-time winner when the striker batted a close-range effort off the line with his hands to earn a red card. 

Not only that, but he ran off celebrating when Asamoah Gyan hit the bar with the resulting penalty. Ghana lost the resulting shoot-out. 

2012: Drogba’s AFCON dream dies

Zambia’s fairytale Africa Cup of Nations win in 2012, their first ever, was a beautiful moment for the winners, but for Ivory Coast it represented rock-bottom as their golden generation fluffed their lines once again. 

Didier Drogba missed a penalty in normal time as a side featuring the likes of Gervinho, Kolo Toure and Yaya Toure fell short at the final hurdle. 

Drogba ended his international career two years later as his country’s all-time top scorer, but without an international trophy.

2014: The Gerrard slip

Steven Gerrard

(Image credit: PA)

Steven Gerrard’s slip on the Anfield turf against Chelsea has gone down as the moment Liverpool lost the 2013/14 title. 

The Reds went into the match five points clear with three games left, but Demba Ba pounced on the error to send the Blues on their way to a 2-0 win, and Brendan Rodgers' side eventually fell to second place.  

Gerrard later called the period “the worst three months of my life” and he would depart Anfield a year later, an all-time great without a Premier League title to show for 17 years of service.

2014: Brazil's semi-final horror show

Things really couldn’t have gone any worse for Brazil in the semi-finals of the 2014 World Cup.

The Selecao, without injured star man Neymar and captain Thiago Silva, were humiliated by Germany in front of their own fans, going 5-0 down in 29 minutes and eventually losing 7-1 in one of the most embarrassing major tournament results ever.

2014: Atleti denied at the death

Atletico Madrid (opens in new tab)’s remarkable rise under Diego Simeone was moments away from reaching the ultimate peak of Champions League glory, only for Sergio Ramos - who else? - to ruin the party.

There would’ve been no sweeter way for Atleti to achieve European glory than by beating their decorated city neighbours in the final, and they were set to do just that until Ramos nodded in a 93rd-minute equaliser.

Simeone’s men collapsed to a 4-1 defeat in extra-time and their wait goes on.

2015: Pirlo's Juventus spell ends in tears

Andrea Pirlo was the epitome of cool on the pitch, but his emotions overpowered him after Juventus (opens in new tab)lost the 2014/15 Champions League final to Barcelona.

Tears streamed down the face of the bearded playmaker, who was denied the ultimate send-off in his final game for the Old Lady.

2016: Camp Nou honours Cruyff

Not many men have had a more lasting impact at a football club than Johan Cruyff at Barcelona (opens in new tab), and the Dutch great’s death in 2016 led to a highly emotional tribute from the Catalan club ahead of an El Clasico match against Real Madrid.

A mosaic of 90,000 cards were raised aloft as the Camp Nou was painted in the club’s colours, an enormous no.14 shirt and the message ‘thank you Johan’.

Johan Cruyff Camp Nou

(Image credit: Getty Images)

2016: Ronaldo ends Welsh run

Wales’ outstanding run to the semi-finals of Euro 2016 will go down in football folklore, but that didn’t make the decisive three-minute blip in their semi-final performance against Portugal any less painful.

Cristiano Ronaldo performed his trademark levitation act to head in the opener, and soon after Nani prodded in Portugal’s second from a cross-shot. Deflating.

2016: Messi retires after fourth final defeat

In the summer of 2016, it felt like there was a curse on Lionel Messi and Argentina. 

The forward missed a penalty in a shoot-out defeat to Chile in the final of the Copa America, extending his country’s wait for silverware to 23 years and leaving a distraught Messi in tears.

There was further pain to come when Messi announced soon afterwards that he would retire from international football, saying “I’ve done all I can” after four final defeats. 

Thankfully, he soon changed his mind – and that elusive Copa America title finally arrived last year.

2016: Independiente del Valle fall at the final hurdle

The Copa Libertadores can be trusted for an upset, but few have matched the remarkable run of Ecuadorian minnows Independiente del Valle, who knocked out giants River Plate and Boca Juniors on their way to the final.

But the team from Quito, who have a 12,000-capacity stadium and whose underdog feats drew comparisons with Leicester’s title win, couldn’t finish off the job against Colombia’s Atletico Nacional, drawing the first leg 1-1 before a 1-0 second leg defeat.

2017: Leicester sack Ranieri

Few moments have underlined the ruthless nature of elite football quite like Leicester’s (opens in new tab)decision to sack Claudio Ranieri nine months after he masterminded the most spectacular of title wins.

The affable Italian was loved and respected by Foxes fans and neutrals alike, and his feat of taking the 5000-1 outsiders to the Premier League crown was extraordinary, so his dismissal left a sour taste in the mouth.

2017: Tears as Totti retires

Rarely, if ever, has a stadium been filled with as much as emotion as on 28 May, 2017: the day Roma (opens in new tab)said goodbye to Francesco Totti.

A local lad, one-club man and one of the greatest talents of his generation, Totti became a Giallorossi icon during his 25-year spell at the club. 

After his final game, a 3-2 win over Genoa, he read a letter to the fans and there wasn't a dry eye in the Stadio Olimpico. Roma’s video of the moment was titled ‘a stadium of tears’. They weren’t exaggerating.

2018: Buffon sees red after Oliver decision

Gianluigi Buffon has won everything there is to win in football – except the Champions League.

Therefore, in his final season with Juventus (opens in new tab), it was particularly painful for him when the Turin club overturned a 3-0 first leg quarter-final defeat to Real Madrid to go 3-3 on aggregate – only for referee Michael Oliver to award the Spaniards a stoppage-time penalty that sent them through.

An infuriated Buffon was sent off for dissent after the decision, and afterwards raged that Oliver had a “rubbish bin instead of a heart”.

2018: Wenger says goodbye to Arsenal

The final home game of Wenger’s 22-year spell in charge of Arsenal was an emotional occasion, as the Frenchman delivered a speech to the Emirates crowd to say goodbye.

“I will always be an Arsenal fan. It is what unites us in every cell of our body, those dreams and worries,” he said.

In came on the back of a difficult campaign in which Wenger came under pressure, but the Gunners faithful were united in their appreciation of one of their all-time greats for his send-off.

2018: The Karius calamity 

Loris Karius was inconsolable when the full-time whistle blew on the 2018 Champions League final, after two absolute howlers from the goalkeeper helped Real Madrid triumph 3-1.

The German rolled the ball directly onto Karim Benzema’s foot for Real’s first, and allowed Gareth Bale’s third to squeeze through his hands. 

You felt for the tearful keeper, who it later transpired was possibly concussed at the time of his costly errors.

2018: Mandzukic ensures it’s not coming home

Agonising only for England fans, perhaps, but the moment Mario Mandzukic scored Croatia’s extra-time winner in the World Cup semi-final will take some time to forget.

After years of hurt since 1966, the Three Lions finally made it to their first semi-final since 1990 under Gareth Southgate. 

But they couldn’t hold on after Kieran Trippier’s early opener, with Ivan Perisic equalising in the second half before Mandzukic ensured that it wasn’t in fact coming home after all.

2019: Ajax's dream run collapses

Ajax became the neutrals’ darlings during the 2018/19 Champions League, as Erik ten Hag’s youthful, exciting side battled all the way from the second qualifying round to the semi-finals.

They knocked out Real Madrid and Juventus to get there and looked set to reach the final after going 3-0 up on aggregate against Tottenham. 

But the final 35 minutes of the tie proved disastrous as Lucas Moura bagged a hat-trick to win it for Spurs on away goals (remember that rule?)

2019: Sissoko's handball

For a team as starved of silverware as Tottenham, reaching the Champions League final was a stunning feat that took them to the brink of the ultimate achievement.

But their plans went up in smoke after just 22 seconds when Sadio Mane lifted the ball onto Moussa Sissoko’s arm, earning the Reds a spot-kick. 

Mohamed Salah scored, and Jurgen Klopp’s men didn’t look back from there.

2019: Bury expelled

After 125 years of English Football League membership, Bury were expelled in August 2019 due to a financial collapse.

A last-gasp deal to rescue the club fell through, resulting in shock and fury as one of England’s oldest clubs was cut adrift, becoming the first team to be kicked out of the EFL since Maidstone United in 1992.

2021: More penalty woes for England

This one was a real sucker punch for the long-suffering Three Lions fans.

England fans have become well accustomed to penalty shoot-out heartache over the years, but at Wembley? In their first major tournament final since 1966? This one stung. 

2021: Messi says bye to Barca

Lionel Messi and Barcelona helped each other reach extraordinary heights over the years, so it's little wonder the Argentine couldn’t keep it together when the time came to say goodbye.

El Pibe was in floods of tears in his final press conference as he explained that he wanted to stay in Catalunya but couldn’t due to the club’s financial plight.

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Alasdair Mackenzie is a freelance journalist based in Rome, and a FourFourTwo contributor since 2015. When not pulling on the FFT shirt, he can be found at Reuters, The Times and the i. An Italophile since growing up on a diet of Football Italia on Channel 4, he now counts himself among thousands of fans sharing a passion for Ross County and Lazio. 

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