England's Euro 2020 final defeat vs Italy ranked as the most heartbreaking since 1990

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England suffered yet more heartache at a major tournament last weekend with a penalty shootout defeat at the hands of Italy in the Euro 2020 final. 

Weeks of hype and expectation culminated at Wembley but Gareth Southgate couldn't avenge his infamous penalty miss at Euro 1996.

Three consecutive missed penalties handed the trophy to the Azzurri and left the Three Lions faithful with that oh so familiar feeling of bitter disappointment. 

It was undoubtedly a tournament of progress which underlined just how far England have come under Southgate's tutelage, but that acknowledge can only do so much to heal the wounds of defeat. 

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Now that the dust has settled on the result, Planet Football have ranked the top 12 most heartbreaking defeats England have suffered since the year 1990. 

Let's take a look at some of the most gut-wrenching results England fans have had to endure. 

12. England 2 Romania 3 – Euro 2000

England needed a point from their final group game at Euro 2000 to progress but, in typical fashion, they conspired to throw away a 2-1 halftime lead. 

Goalkeeper Nigel Martyn was at fault for Romania's equaliser before Phil Neville gave away a late penalty, which was converted by Ionel Ganea to knock England out.  

11. England 1 Iceland 2 – Euro 2016

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Every England fan will be in a hurry to forget his one. 

A last-16 tie against Iceland looked like a routine victory on paper, and Wayne Rooney's 4th-minute penalty appeared to put the Three Lions on course for a heavy win.

However, the Icelandic minnows turned the game on its head with two goals inside 14 minutes and England offered little by way of attacking response thereafter.

The players, visibly stunned by their situation, could barely spring a few passes together for large parts of the game and limped out of the tournament in humiliating circumstances. 

10. Norway 2 England 0 – World Cup 1994 qualifying

England's first loss in a World Cup qualifier for 12 years arrived on Norwegian soil. 

Graham Taylor's switch to a back-three didn't pay off and England's 2-0 defeat eventually cost them a place at the 1994 World Cup.

9. England 2 Croatia 3 – Euro 2008 qualifying

Look away now, Scott Carson. 

Steve McClaren opted to select Carson between the sticks and the young stopper made an absolute howler to allow Niko Kranjcar's long-range strike to squirm through his grasp and hand Croatia an early 1-0 lead. 

England rallied but failed to overturn the deficit and didn't qualify for Euro 2008 as a result. 

8. Germany 4 England 1 – World Cup 2010

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Frank Lampard's infamous ghost goal and that foot race between Gareth Barry and Mesut Ozil will live long in the memory. 

England crashed out of the World Cup at the last-16 stage in truly humbling circumstances as Germany exerted their yawning superiority to coast to a 4-1 win. 

The goal that never was from Lampard was merely a footnote in what would have inevitably been a German victory - even if the officials had correctly adjudged the ball to have been over the line. 

7. England 1 Croatia 2 – World Cup 2018

England found themselves in unfamiliar territory at the 2018 World Cup when they navigated beyond Colombia and Sweden in the knockout rounds to set up a semi-final tie with Croatia. 

It was a winnable clash on paper and Kieran Trippier's stunning 5th minute free-kick looked to send England, and their charming waistcoat-clad manager, on their way to the showpiece final.

However, Ivan Perisic grabbed a deserved equaliser in the second half and in truth there only looked like one winner from that moment. 

Mario Mandzukic sunk England dreams in extra-time with a sucker punch beyond Jordan Pickford.

Back to reality. 

6. Portugal 2 England 2 (6-5 on pens) – Euro 2004

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One of the great penalty shootouts in history featured a gloveless goalkeeper. 

England were fancied to go far at Euro 2004 with their talented roster of players, but succumbed to the sheer fearlessness of Portugal's Ricardo, who saved a Darius Vassell penalty with his bare hands before stepping up to slam the winning strike home himself.

A stunning slice of international tournament football history.

5. Portugal 0 England 0 (3-1 on pens) – World Cup 2006

Familiar foes once again proved to be England's nemesis.

Frank Lampard, Steven Gerrard and Jamie Carragher all missed penalties in a game that signalled the end for Sven Goran Eriksson's time in charge. 

4. England 2 Argentina 2 (3-4 on pens) – World Cup 1998

Sensing a theme here? England and penalties don't go hand in hand. 

David Beckham made himself a national villain after getting himself sent off for a petulant kick out at Diego Simeone, and the game eventually was decided when David Batty missed England's 5th and final penalty in the shootout. 

3. England 1 West Germany 1 (3-4 on pens) – World Cup 90

More semi-final and penalty heartache for England was drowned in Paul Gascoigne's tears.

Gazza was booked in extra-time and the waterworks opened with the realisation that he would be suspended for the final.

It wasn't to matter as England crashed out following penalty misses from Stuart Pearce and Chris Waddle, who smashed his effort over the crossbar. 

2. England 1 Germany 1 (5-6 on pens) – Euro 96

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Arguably the most replayed failure in England's history.

As the hosts of Euro 96, Terry Venables' side were backed to the tilt by 75,000 fans at Wembley in the semi-final, but Southgate eventually came to be the depiction of failure when he missed England's 6th penalty. 

Everyone before him had converted their spot kicks and his miss gave Andreas Moller the opportunity to secure Germany's place in the final.

He crashed the ball into the roof of the net emphatically and quashed the perennial dream of bringing football home. 

1. England 1 Italy 1 (2-3 on pens) – Euro 2020

Euro 2020 wasn't a home tournament for England, but it was about as close as you could get to one without officially getting the honour. 

Southgate's side navigated their way into the showpiece final at Wembley with ruthless conviction, boasting one of the most talented and upstanding squad of players in the nation's history.

All the ingredients were in place for England to finally end their 55-year wait for a major trophy, but they once again fell short in a penalty shootout. 

Jordan Pickford was heroic, saving two penalties from Ciro Immobile and Jorginho, but Marcus Rashford, Jadon Sancho and Bukayo Saka missed three penalties in a row as Southgate faced a familiar feeling of penalty shootout dejection. 

The result will sting for months but England can be immensely proud of what they achieved at Euro 2020.

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