England’s TEN biggest European Championship heartbreaks as they look to end poor run at Euro 2020

England have suffered plenty of heartbreak since winning the World Cup in 1966, yet curiously some of their biggest soul-crushing failures have come at the European Championship.

At least the Three Lions have gone all the way on the global stage. England have never won the Euros and have a wretched record at the finals even if a team of stars with the best preparation turn up with ‘realistic’ intentions to win it.

As Gareth Southgate’s team head into Euro 2020 finally looking to end a nation’s 55-year wait for silverware, Sportsmail looks at the 10 biggest heartbreaking moments from the Euros which have prevented football coming home.

England players react after losing against Germany on penalties during the Euro 96 semi-finals

ENGLAND AT THE EUROS 

1960 – Did not enter

1964 – Did not qualify

1968 – Third place 

1972 – Did not qualify

1976 – Did not qualify 

1980 – Group stage

1984 – Did not qualify

1988 – Group stage

1992 – Group stage

1996 – Semi-finals

2000 – Group stage

2004 – Quarter-finals

2008 – Did not qualify

2012 – Quarter-finals

2016 – Last-16 

10. England 2-3 Portugal – Euro 2000

England had stumbled their way into Euro 2000, finishing a distant second in their qualifying group behind Sweden, and then limping past Scotland in the play-offs by hanging onto a 1-0 defeat at Wembley to progress 2-1 on aggregate. 

Euro 2000 was noteworthy for having an incredibly strong lineup at the tournament and there were no easy groups, with England pitted against Portugal, Germany and Romania – the latter two having beaten them in the previous two major tournaments.

Manager Kevin Keegan was blessed with an attacking squad but, to put it kindly, never really organised a system to protect a decent but very vulnerable back four, with his squad selections code for ‘If you score three, we’ll score four.’

Nuno Gomes completed Portugal's turnaround as he fires past Tony Adams and David Seaman

Nuno Gomes completed Portugal’s turnaround as he fires past Tony Adams and David Seaman

So in England’s opening game in Eindhoven, Keegan left a 33-year-old Paul Ince to deal with Portugal’s dangerous front four of Joao Pinto, Luis Figo, Nuno Gomes and Manuel Rui Costa… and for 20 minutes it was paying off.

Paul Scholes and Steve McManaman had helped England race into a deserved 2-0 lead following typical sublime crosses from David Beckham and Portugal were rocking.

But in the 22nd minute Figo pulled one back with a deflected effort from long range after cantering through no-man’s land where England’s defensive midfield should have been, and just over five minutes before the break Pinto’s smart header across goal produced an equaliser.

England wilted after the break and the turnaround was completed just short of the hour mark when Gomes stabbed home. Scholes missed a good chance to equalise with a header but once again the hopes of a nation were dashed in little over an hour. 

Dejected England boss Kevin Keegan looks on

Alan Shearer and Paul Scholes (right) react to their opening game defeat by Portugal at Euro 2000

Dejected England boss Kevin Keegan looks on as Alan Shearer and Paul Scholes (right) react to their opening game defeat by Portugal at Euro 2000

9. England 0-1 Republic of Ireland – Euro 88

There was plenty of optimism for England heading into Euro 88. The side had started to click under Bobby Robson having reached the quarter-finals of the previous World Cup where they were only denied a semi-final spot courtesy of some handy work by one Diego Maradona.

But even recent form had been good, they comfortably topped their qualifying group unbeaten with five wins from six and a record of 19 goals scored and one conceded.

Still, with a group consisting of Republic of Ireland, Holland and the Soviet Union, Robson believed his side needed a confidence boost heading into the tournament… so he set up a pre-tournament friendly against non-league side Aylesbury, and it was no surprise to see his side run out 7-0 winners. 

England faced a crucial opening game against Republic of Ireland, knowing defeat would leave them under huge pressure to qualify for the semi-finals, ahead of a meeting with a deadly Holland attack spearheaded by a peak Marco van Basten.

England were favourites to defeat Republic of Ireland in their opening group game at Euro 88

England were favourites to defeat Republic of Ireland in their opening group game at Euro 88

Robson’s side were tipped to go through with the Dutch and were big favourites to see off Ireland. Brian Clough, who had a habit of inadvertently doing the team talk for England’s opposition, insisted as a TV pundit before the game that the likes of Gary Lineker and Peter Beardsley would be ‘rubbing their hands’ with glee at the prospect of facing the Irish defence.

But it took just six minutes for England’s trip to West Germany that summer leaving them thinking they should have stayed in Aylesbury instead.

Ray Houghton gave Jack Charlton’s side a shock lead in Stuttgart, which they held on to for the rest of the game to give his outfit a very famous win and leave a previously confident England side crestfallen.

They never recovered. Three days later they were beaten by the Dutch 3-1 to be eliminated and the ultimate humiliation was complete when they were then also beaten 3-1 by the Soviet Union in their final game. With a 100 per cent defeat record from three games, Euro ’88 is officially England’s worst ever showing at a major tournament.

But Ray Houghton's header in Stuttgart inflicted a defeat that England never recovered from

But Ray Houghton’s header in Stuttgart inflicted a defeat that England never recovered from

8. England 1-2 France – Euro 2004

England travelled to Portugal confident they could progress far in the tournament, although wary that similar past expectations were soon met with a metaphorical custard pie to the face.

But they were given a tough task in their opening game of the competition up against holders and pre-tournament favourites France who boasted the likes of Thierry Henry, Patrick Vieira and Zinedine Zidane.

England were slight underdogs in Lisbon but battled well in the first half and even took the lead when Frank Lampard headed in a Beckham free-kick.

David Beckham sees his second half penalty saved by France goalkeeper Fabien Barthez

David Beckham sees his second half penalty saved by France goalkeeper Fabien Barthez

Sven Goran Eriksson had a secret weapon in his attack, with a fresh faced Wayne Rooney causing havoc to the French defence. He won a penalty in the second half after leading a counter attack, only for Beckham to see his spot-kick saved from 12 yards by Fabien Barthez.

Still, it didn’t look like it would matter. England looked like they had got the job done when after 90 minutes they were still leading 1-0 and on course for a huge statement win having nullified one of Europe’s best attacks.

Yet as the clock ticked over into stoppage time, Zidane equalised with an excellent free-kick from 25 yards.

But the frustration turned into a nightmare, 90 seconds later Steven Gerrard’s horrendous back pass forced David James to bring down Henry in the box and with effectively the last kick of the match Zidane made no mistake from the penalty spot to inflict defeat on England – whose sudden implosion was incredible even by their slapstick standards at major tournaments. 

As the game entered stoppage time, Zinedine Zidane equalised for France with a free-kick

As the game entered stoppage time, Zinedine Zidane equalised for France with a free-kick

Zidane then scored again from the spot as Beckham looks on dejected at the end of the game

Zidane then scored again from the spot as Beckham looks on dejected at the end of the game

7. England 2-3 Croatia – Euro 2008 qualifier

At the 2006 World Cup in Germany there was much hype for England’s so-called ‘golden generation’ to go on and finally end 40 years of hurt.

A weak quarter-final exit to Portugal followed but the real nightmare was to come just over a year later while trying to qualify for Euro 2008.

Steve McClaren had stepped up from assistant to Eriksson to replace the Swede after the World Cup and did little to appease an already underwhelmed public when he axed England captain David Beckham from his squad.

Yet, the mood somehow got darker when after five games, including a defeat in Croatia and draws against Macedonia and Israel, England were struggling to qualify from a group where the top two went through.

Goalkeeper Scott Carson allowed a long range shot from Croatia's Niko Kranjcar (not pictured) to slip past him in the Wembley rain to leave England on the back foot early in the game

Goalkeeper Scott Carson allowed a long range shot from Croatia’s Niko Kranjcar (not pictured) to slip past him in the Wembley rain to leave England on the back foot early in the game

A brief revival (including a Beckham recall) saw them head to Russia with two games to go knowing one more win would seal their Euro 2008 place, only to throw away a 1-0 lead via a Wayne Rooney strike to lose 2-1 courtesy of a Roman Pavlyuchenko double.

So, a Wembley tie against an already qualified Croatia followed, with a draw enough to secure qualification. What could possibly go wrong?

McClaren’s surprise call to start Scott Carson in goal soon backfired when he allowed a long range Niko Kranjcar shot to slip past him early on, while Ivica Olic added to leave England 2-0 down inside 15 minutes in the Wembley downpour.

England rallied after the break via a Frank Lampard penalty and a Peter Crouch equaliser to leave them back on course for the finals, only for Mladen Petric to restore Croatia’s lead with 13 minutes to play and divert England on the road to nowhere but humiliation and without a ticket to the Euros, with McClaren departing soon after.

England came from 2-0 to equalise but still fell to a 3-2 defeat as they failed to qualify

England came from 2-0 to equalise but still fell to a 3-2 defeat as they failed to qualify

England manager Steve McClaren departed after failing to qualify for Euro 2008

England manager Steve McClaren departed after failing to qualify for Euro 2008

6. England 1-2 Sweden – Euro 92 

A stark warning to the England team today that even with a positive World Cup experience behind you, the European Championship has no respect for past form.

Admittedly, England’s 1992 squad for the trip to Sweden looked much different to the ageing side that reached the semi-finals of Italia ’90 and there was even a new manager with Graham Taylor having replaced Bobby Robson.

Key injuries had decimated England’s spine too, with Mark Wright, John Barnes and Paul Gascoigne all ruled out while Taylor had controversially dropped Italia ’90 stars like Chris Waddle and Peter Beardsley.

It wasn’t all bad luck though. In the eight-team tournament of two groups, England managed to avoid Germany and a handy Scotland team and were put in a section with Sweden, France and Yugoslavia – who would eventually be replaced by Denmark.

Gary Lineker's international career came to a miserable end when he was substituted by Graham Taylor with England trying to restore the lead they needed to reach the semi-finals

Gary Lineker’s international career came to a miserable end when he was substituted by Graham Taylor with England trying to restore the lead they needed to reach the semi-finals

England laboured through the group stages though and after goalless draws against Denmark and France needed to beat the host nation to guarantee a semi-final spot.

By half-time they were top of the group in Solna, courtesy of a fourth minute opener from David Platt. But the Three Lions then endured one of their most miserable 45 minutes in the modern era.

Jan Eriksson equalised shortly after half-time and with half-an-hour to go Taylor controversially took off captain Gary Lineker, who was retiring after the tournament and just one goal away from equalling Bobby Charlton’s English record of 49 goals, replacing him with Alan Smith.

England needed to score again but with eight minutes left Thomas Brolin won the ball in midfield, played a slick one-two with Martin Dahlin and from the edge of the box stabbed at the ball (and a collective English nation’s heart) with a first-time finish that looped over Chris Woods. England had gone from top to bottom of the group and ended their Euro adventure with a record of zero wins and just one goal. 

But a moment of magic from Thomas Brolin inflicted defeat on England to dump them out

But a moment of magic from Thomas Brolin inflicted defeat on England to dump them out

5. England 1-2 Iceland – Euro 2016

The first of the expanded European Championships to 24 teams was good news for England, as it meant their often troubled path through the group stage would mean that even they could seemingly progress with few battle wounds.

Yet this new format where even a few best performing third place teams could reach the knockout stages still left England with some scarring – at least mental ones – as they limped into the last-16.

Once again they failed to win their opening game, after Eric Dier’s late free-kick was cancelled out by a stoppage time equaliser from Russia. Although in their next game a stoppage time Daniel Sturridge goal saw them come from behind to defeat Wales after Jamie Vardy had cancelled out a Gareth Bale opener.

So the brief before the Slovakia game was simple. Win and they topped the group, giving them in theory a slightly easier run to the final. Anything else and they were risking potential quarter-finals with hosts France and a semi-final with either Germany, Spain or Italy.

Iceland's Ragnar Sigurdsson fires past England keeper Joe Hart to equalise in the sixth minute

Iceland’s Ragnar Sigurdsson fires past England keeper Joe Hart to equalise in the sixth minute

Roy Hodgson sent out a weakened team, including dropping key men Harry Kane and Wayne Rooney, and paid the price with a lifeless goalless draw which left them second in the group behind Wales following their inspired 3-0 victory over Russia.

The hard way it was then for England, but first they at least had an ‘easy’ last-16 clash with Iceland to overcome in Nice.

Four minutes in and with the big boys back in the side all was seemingly normal again as Rooney dispatched a fourth minute penalty. Yet 15 minutes later and England were left stunned after falling 2-1 down.

Roy Hodgson’s side had over 70 minutes to respond yet incredibly for the rest of the match hardly created a single chance as they froze like rabbits in the headlights. Once the final whistle came a nation responded with anger rather than sadness at their latest tournament calamity and Hodgson paid the ultimate price by resigning as manager just minutes after the final whistle.

Devastated England players react following their shock last-16 defeat by Iceland in Nice

Devastated England players react following their shock last-16 defeat by Iceland in Nice

After a disastrous tournament, Roy Hodgson resigned minutes after the final whistle

After a disastrous tournament, Roy Hodgson resigned minutes after the final whistle

4. England 0-0 Italy (2-4, PENS) – Euro 2012

It has counted for little in the past but England often head into tournaments off the back of strong qualifying campaigns that gave reasons to be optimistic.

The trip to Poland/Ukraine was different though. Although Fabio Capello had guided his side through the qualification stages with little fuss, he stood down four months before the tournament. The Italian was enraged that the FA decided to remove John Terry of the captaincy, with the defender due in court having been charged with racially abusing Anton Ferdinand – a charge he was later cleared of.

Roy Hodgson was named as Capello’s surprise replacement ahead of Harry Redknapp, but there was little fanfare regarding England’s chances – especially with France first up again followed by games with Sweden and co-hosts Ukraine.

To dampen expectations further, star-man Rooney was suspended for two matches following a red card in England’s final qualifier for the tournament.

Danny Welbeck vies for the ball with Andrea Pirlo, who scored a great Panenka in the shootout

Danny Welbeck vies for the ball with Andrea Pirlo, who scored a great Panenka in the shootout

England though performed well in the group, gaining a credible 1-1 draw with France, coming from 2-1 down to beat Sweden and then seeing off Ukraine – with Rooney scoring on his return – to reach the quarter-finals as group winners where they would face Italy in Kiev.

For the opening 20 minutes England went toe-to-toe with Italy but as the game wore on they become under increasing pressure and their only answer to Andrea Pirlo orchestrating the midfield was to hit hopeful long balls to Andy Carroll.

An Italy goal looked inevitable, but even after extra-time it never came and although England had a dreadful shootout record, Italy’s past record from 12 yards was not much better.

A place in the semi-finals against Germany suddenly beckoned, especially when England led on penalties after a Riccardo Montolivo miss. Then Pirlo’s Panenka somehow changed the complexion of the shootout, with Ashley Cole and Ashley Young both missing leading to the Three Lions being dumped out on spot kicks at the European Championship finals for the third time in their last four appearances.

With Italy on the ropes in the shootout, Andrea Pirlo's Panenka changed the mood of the tie

With Italy on the ropes in the shootout, Andrea Pirlo’s Panenka changed the mood of the tie

England failed to score any of their remaining penalties as they were eliminated in Kiev

England failed to score any of their remaining penalties as they were eliminated in Kiev

3. England 2-3 Romania – Euro 2000

Having opened with a 3-2 defeat by Portugal there were positives and negatives for England at the start of Euro 2000 co-hosted by Holland and Belgium. While they were looking flaky and disjointed at back, they had displayed a clear threat in attack.

They were going to need that attack too as in their next game a defeat against their old rivals and holders Germany would have seen them make a familiar group stage departure on foreign soil.

However, fortune favoured Keegan’s side as the Germans, having drawn 1-1 in their opener with Romania, were at one of their lowest ebbs in history with much of their stars from Euro ’96 having retired (Jurgen Klinsmann) or at the very least were well past their best (Lothar Matthaus).

Dorinel Munteanu (right) of Romania celebrates equalising at the start of the second half

Dorinel Munteanu (right) of Romania celebrates equalising at the start of the second half 

England took advantage. In an otherwise poor game, Alan Shearer’s second half header from Beckham’s third cross and assist of the tournament took the three points and left them needing only a draw against Romania to progress.

There was more chance of Keegan coming out of retirement to join Shearer and Michael Owen in attack than the England boss playing it cautious and at half-time the usual attacking approach was paying off as in five minutes before the break Shearer and Owen helped the Three Lions come from behind to lead in Charleroi.

Yet, no one was fooled. England had been poor throughout the first period and could have counted themselves fortunate to be level let alone winning the game.

A wake up call was needed but it never came as Romania equalised at the start of the second half and maintained pressure throughout the final 45 minutes.

England though looked like they would hang on with a 2-2 draw to progress… until Phil Neville’s wild and desperate sliding tackle on Viorel Moldovan with a minute to go enabled Ionel Ganea to dispatch from the penalty spot and leave Keegan’s talented but naive side catching another early flight home along with Germany.

IoanI Ganea of Romania scored the winning goal from the penalty spot with just a minute to go

IoanI Ganea of Romania scored the winning goal from the penalty spot with just a minute to go

Beckham (7) and Martin Keown (6) look to console Phil Neville at full-time after his foul led to the spot-kick that would see England eliminated at the group stage of Euro 2000

Beckham (7) and Martin Keown (6) look to console Phil Neville at full-time after his foul led to the spot-kick that would see England eliminated at the group stage of Euro 2000

2. England 2-2 Portugal  (5-6, PENS) – Euro 2004

England had responded well after their catastrophic collapse against France, with Rooney continuing to star with a double brace to help defeat Switzerland and Croatia, underlining the striker as one of the tournament’s stand out performers.

The Three Lions had set a marker heading into the quarter-finals where a tough prospect in hosts Portugal were waiting for them in Lisbon. But England were playing some of their finest football under Eriksson and had good reason to be confident against a side fielding a formidable lineup including Figo, Deco, Gomes and even a young Cristiano Ronaldo.

An opportunistic effort from Owen gave them the lead inside four minutes but disaster struck when Rooney was forced to limp off injured later in the first half with a broken foot.

From then on England looked blunt and spent much of the rest of the game holding on until with just seven minutes to play, Tottenham Hotspur flop Helder Postiga diverted in a cross to equalise.

Sol Campbell's (6) header in the final minute for England was controversially disallowed after John Terry was penalised for a foul on Portugal keeper Ricardo

Sol Campbell’s (6) header in the final minute for England was controversially disallowed after John Terry was penalised for a foul on Portugal keeper Ricardo

David Beckham blames the penalty spot after blasting over his penalty kick in the shootout

David Beckham blames the penalty spot after blasting over his penalty kick in the shootout

England though went straight on the attack and in the final minute Sol Campbell had a close range header controversially disallowed following an apparent push by centre-back partner John Terry on goalkeeper Ricardo.

High drama followed as the game went into extra-time. Substitute Rui Costa put Portugal ahead with 10 minutes to play after gliding past Phil Neville, who perhaps learned too much from four years earlier by making a woeful attempt to challenge the midfielder.

Still, England found resolve and Frank Lampard controlled a John Terry knockdown before blasting home with five minutes left to take the game to penalties.

Then the familiar demons returned, with Beckham once again failing from 12 yards by comically firing way off over the bar – blaming the turf on the penalty spot in the process. Rui Costa though also missed but as the shootout went into sudden death, Ricardo’s bizarre gamesmanship saw him take off his gloves to save Darius Vassell’s spot-kick before immediately stepping up and slotting home the winner to dump England out of the tournament in gut-wrenching fashion.

After taking off his gloves, Ricardo saved Darius Vassell's penalty in sudden death

After taking off his gloves, Ricardo saved Darius Vassell’s penalty in sudden death

The Portugal keeper then stepped up to fire past David James and dump out England

The Portugal keeper then stepped up to fire past David James and dump out England

1. England 1-1 Germany (5-6, PENS) – Euro 96 

There is though no doubt over England’s biggest heartbreak in the history of the European Championship – Euro ’96 really was the tournament they looked so, so close to winning and remains to this day arguably the best opportunity they have had to lifting a major trophy since 1966.

It was the summer where a nation almost on a loop was singing ‘Football’s coming home’, as England finally seemed to return as a force following a relative six years in the doldrums. Shearer and Teddy Sheringham were clicking in attack, Paul Ince and Paul Gascoigne were midfield generals and England’s back four had never looked so secure.

But even with Euro ’96 on home soil, England’s usual party trick of stumbling out the blocks could not be avoided after a 1-1 draw with Switzerland. Then Terry Venables’ team took off – beating Scotland 2-0 courtesy of a wonder goal from Gascoigne before putting in one of the best ever Three Lions showings by dismantling Holland 4-1.

With the chance to score the winning goal, Darren Anderton (11) hit the post for England

With the chance to score the winning goal, Darren Anderton (11) hit the post for England 

Paul Gascoigne then missed out sliding home a winning goal against Germany by mere inches

Paul Gascoigne then missed out sliding home a winning goal against Germany by mere inches

Gascoigne at full stretch was unable to connect with Shearer's bobbling volley across the box

Gascoigne at full stretch was unable to connect with Shearer’s bobbling volley across the box

A nervous display against Spain followed in the quarter-finals, but a goalless draw was followed by a penalty shootout win as Stuart Pearce made up for his spot-kick horror at the 1990 World Cup and David Seaman denied Miguel Nadal to send England into a semi-final with Germany.

England had played all their games at Wembley and the stadium was rocking when tournament top scorer Alan Shearer headed home in the third minute, only for Stefan Kuntz to equalise 13 minutes later. In a tight game, the scores remained that way heading into extra time.

New for Euro ’96 was Golden Goal, with the concept being the first to score in an allotted 30 minute period would win the game, in a bid to promote attacking play in the additional period.

England went agonisingly close to doing just that – twice. The first resulted in Darren Anderton turning a low cross from Steve McManaman against the post yet still the real heartbreaker was to come.

Gareth Southgate's penalty is saved by Germany keeper Andreas Kopke in the shootout

Gareth Southgate’s penalty is saved by Germany keeper Andreas Kopke in the shootout

Southgate reacts following his sudden death miss

After the semi-final defeat he is consoled by goalkeeper David Seaman

Southgate’s miss proved costly as it led to a shootout defeat and a semi-final loss at Wembley

Andreas Moller celebrates after scoring the winning penalty to send Germany into the final

Andreas Moller celebrates after scoring the winning penalty to send Germany into the final

Shearer’s low volley trickled across the six-yard box and only needed a tap in from Paul Gascoigne to steer England into the final. Yet at full stretch he missed by no more than a few millimetres in making contact as a nation gasped and buried their collective heads into their hands. Watching it now, you can still be convinced one day he will score it.

Germany survived so to penalties it went, and as shootouts go you may never see a better quality one, with both sides scoring all five and England sending all their spot-kicks into the top right corner. Gareth Southgate stepped up next though in sudden death and in electing bottom left could only find Andreas Kopke.

Andreas Moller hit the final nail in the coffin by scoring the winning penalty and with England fans still distraught at seeing their hopes of football coming home dashed having come so close, they then had to watch the German midfielder’s mocking hands on hip celebration for good measure.