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Since their World Cup triumph in 1966, England have become synonymous with heartbreaking defeats on the grandest stages. In true English fashion, we’ve compiled and ranked the 14 most painful losses that have defined decades of national footballing anguish.

We often remind ourselves not to expect too much from England at major tournaments, yet every time one arrives, hope inevitably creeps in — only to be crushed once more.

Sadly, that means this list will likely keep growing for years to come.

“Another wretched night for England at a major tournament,” sighed commentator Clive Tyldsley after the Three Lions’ latest humiliation. It was arguably their most dispiriting showing; few had high expectations for Roy Hodgson’s men, yet their surrender was so meek it brought deep embarrassment to the shirt.

Only Marcus Rashford injected any calmness or sharpness, though he came on with just four minutes to play.

The scene at full-time told the story: players sprawled across the Iceland box after a failed corner, Joe Hart among them, his weak hands once again the subject of ridicule as he offered yet another awkward apology.

Earlier, dropped points against Norway meant England had to win in Rotterdam, where refereeing decisions contributed heavily to their downfall — costing the team a World Cup berth and Graham Taylor his job.

Ronald Koeman escaped with just a yellow card for dragging down David Platt, then rubbed salt in the wound by scoring from the ensuing free-kick. The Netherlands added another, effectively ending England’s hopes with a game still to play.

After a string of near-misses that could be blamed on misfortune rather than incompetence, Steve McClaren arrived and reminded everyone of England’s capacity for chaos. Needing only a draw to reach Euro 2008, McClaren dropped Paul Robinson and David Beckham. “I thought Scott Carson was ready and I stand by that decision,” he explained after watching the young keeper’s early blunder gift Croatia a 2-0 lead.

Beckham came off the bench at half-time, his cross finding Peter Crouch for an equaliser that briefly offered hope. But from beneath his infamous umbrella, McClaren watched Mladen Petric fire a 77th-minute winner for Croatia, eliminating England and destroying his own reputation in the process.

McClaren’s successor Fabio Capello ensured qualification for the next tournament, but the 2010 World Cup in South Africa brought fresh humiliation. England struggled through a group featuring Algeria, the United States, and Slovakia, so perhaps the heavy defeat to Germany in the Round of 16 was predictable.

Frank Lampard’s disallowed ‘goal’ provided a convenient excuse, but it did little to disguise the gulf in class. Germany barely needed to exert themselves to dismantle one of the slowest England sides ever assembled.

England’s entire 2018 World Cup run felt dreamlike — a likeable squad, a manager in a waistcoat who seemed one of us — and then, miraculously, a penalty shootout victory. When Kieran Trippier scored that free-kick against Croatia, belief surged across the nation.

But it was not to be. Croatia’s Ivan Perisic equalised, and in extra-time, Mario Mandzukic delivered the fatal blow. It felt more merciful than the emotional batterings England fans had grown used to enduring.

At Euro 2024, Gareth Southgate’s men advanced through the rounds with all the grace of an elephant in a paddling pool before being systematically outplayed by Spain. Cole Palmer’s equaliser briefly lifted spirits, but Spain calmly restored their lead before extra-time, sealing England’s exit.

The 4-1 thrashing by Germany in 2010 marked the end for the so-called ‘Golden Generation.’ Six years earlier, fans had dared to dream again as Wayne Rooney burst onto the scene at Euro 2004. Two group wins set up a quarter-final against hosts Portugal. Michael Owen’s early goal raised hopes, but Rooney’s injury midway through the first half changed everything. Portugal equalised late, Sol Campbell had a goal disallowed, and extra-time led inevitably to penalties. Beckham slipped, Darius Vassell’s shot was saved by Ricardo — who then scored himself to finish the job.

“Three of England’s penalty takers failed with attempts in which the slackness of their body language spoke of men who were ready to put their trust in the belief that their reputations alone would be enough,” wrote The Guardian in a damning verdict. Two years later, at the 2006 World Cup, England once again fell to Portugal — this time after Wayne Rooney’s red card and another shootout disaster, with Lampard, Steven Gerrard, and Jamie Carragher all missing. It was the end of Sven-Goran Eriksson’s reign and the death of another generation’s dreams.

Fast forward to Qatar 2022, and England again fell short. Harry Kane’s missed penalty against France will haunt him, as England fell 2-1 in a match they could have won. With a semi-final against Morocco beckoning, the chance of a World Cup final slipped agonisingly away.

Another classic, more misfortune, more heartbreak. In Saint-Etienne in 1998, England and Argentina traded early penalties before 18-year-old Michael Owen scored a wonder goal, slicing through the defence to put England ahead. But as always, it unravelled. Javier Zanetti equalised, then Beckham was sent off for kicking out at Diego Simeone. A disallowed Sol Campbell winner and another penalty shootout defeat sealed their fate. David Batty, who had never taken a penalty before, missed the decisive kick.

“He told me he’d never taken one before, but it didn’t matter,” recalled manager Glenn Hoddle. Of course, it did. England were out — again.

In 2026, it happened once more. England led Argentina through Anthony Gordon’s goal but retreated too early. Argentina struck late to win, leaving England five minutes from a World Cup final and shattered once again. Thomas Tuchel may have been on the bench, but this collapse had Southgate’s fingerprints all over it.

The 1990 World Cup in Italy set the template for all future heartbreaks. Criticised early, Sir Bobby Robson’s side rallied to reach the semi-finals, inspired by Paul Gascoigne. Against West Germany, they led the play but conceded a cruel deflection off Paul Parker. Gascoigne’s yellow card meant he’d miss the final; Peter Shilton’s slow reactions in the shootout sealed their exit as Stuart Pearce and Chris Waddle missed from the spot.

It took years to recover from Turin. Six years later, at Euro 96 on home soil, England looked destined to end their long wait. After beating Scotland and demolishing the Netherlands, they edged Spain on penalties and faced Germany in the semis. Alan Shearer scored early, but Stefan Kuntz equalised. Gazza’s near-miss in extra-time and Darren Anderton’s shot off the post still haunt fans to this day. When Gareth Southgate missed his penalty, Andreas Möller’s celebration rubbed in the pain. Football so nearly came home.

After the 2018 semi-final run, England went one better at the delayed Euro 2020, reaching the final at Wembley. Luke Shaw’s second-minute goal had fans dreaming, but Leonardo Bonucci equalised, and penalties loomed once more. Despite Jordan Pickford’s two saves, misses from Marcus Rashford, Jadon Sancho, and Bukayo Saka handed Italy the title. Another chapter of sorrow was written into England’s long history of heartbreak.