England's most heartbreaking World Cup exits - ranked

James Cormack
Harry Kane missed a crucial penalty which saw England exit the 2022 World Cup
Harry Kane missed a crucial penalty which saw England exit the 2022 World Cup / James Williamson - AMA/GettyImages

England have become synonymous with World Cup heartbreak since 1966 and supporters were forced to endure more pain as the loveable Three Lions crashed out of the 2022 iteration of the tournament to France in the quarter-finals.

The manner of their defeat ignited the pain for long-suffering English supporters who have gone so long without seeing their country taste glory on the grandest stage.

Defeat to the French was tough to stomach given the context and how the contest played out, but where does it rank among England's most heartbreaking World Cup exits?

6. Quarter-final vs West Germany (Mexico 1970)

England's defence of their World Cup crown started promisingly in the Mexican heat as they progressed into the quarter-finals following victories over Romania and Czechoslovakia in the group stage.

A vengeful West Germany awaited in the last eight but it was the 1966 victors who seemed destined to advance as they had a 2-0 lead with 20 minutes remaining.

However, a Franz Beckenbauer goal completely altered the dynamic of the contest as Uwe Seeler grabbed the equaliser in the 81st minute. Shellshocked heading into extra time, England eventually succumbed to a Gerd Muller strike in what was Sir Bobby Charlton's final game for the Three Lions.

5. Quarter-final vs Portugal (Germany 2006)

Wayne Rooney
Wayne Rooney was sent off in England's quarter-final defeat to Portugal in 2006 / Tom Jenkins/GettyImages

This might have been the most talented England squad we'd ever seen. The Golden Generation's apex.

However, the Three Lions flattered to deceive for the most part in 2006 as they stumbled into the quarter-finals following a round of 16 victory over Ecuador.

A big performance was promised against Portugal by manager Sven-Goran Eriksson, but England displayed little else other than guts to take the contest to penalties after Wayne Rooney was sent off on the hour.

They never came close in the shootout, though, as Ricardo saved three penalties to help Portugal into the semi-finals and draw the curtain on Eriksson's tumultuous reign.

4. Round of 16 vs Argentina (France 1998)

David Seaman, Roberto Ayala
England were beaten on penalties by Argentina in 1998 / PATRICK KOVARIK/GettyImages

While this defeat occurred early on in the 1998 knockout stages, England had come so close to beating old foes Argentina against all the odds.

This was a thrilling encounter that had it all, including Michael Owen's sequence of majesty, a savvy free-kick routine and David Beckham's moment of petulance.

Beckham's dismissal left England with ten men but they thought they'd taken a 3-2 lead with ten minutes remaining when Sol Campbell nodded home Darren Anderton's corner. The jubilant defender ran off in celebration only to discover that referee Kim Nielsen had ruled the goal out for Alan Shearer's phantom foul on goalkeeper Carlos Roa.

Glenn Hoddle's side held out for penalties but were beaten in the shootout when Roa saved David Batty's spot kick.

3. Semi-final vs Croatia (Russia 2018)

Mario Mandzukic, Jordan Pickford
Mario Mandzukic broke English hearts in 2018 / Fred Lee/GettyImages

Following years of indifference and underperformance, England arrived at the 2018 World Cup with relatively low expectations.

Winning their first knockout game at the tournament since 2006 was the aim and they'd complete their goal with the utmost irony: by winning on penalties.

Sweden were brushed aside in the quarters before Kieran Trippier sent the nation into raptures by beating Croatia goalkeeper Danijel Subašić with an unforgettable free-kick in the opening exchanges of their first World Cup semi-final since 1990.

A wily Croatia outfit soon seized control, however, and their victory appeared inevitable when Ivan Perisic equalised with over 20 minutes remaining. Eventually, it was Mario Mandzukic who sunk the dagger into English hearts in extra time.

2. Quarter-final vs France (Qatar 2022)

England v France: Quarter Final - FIFA World Cup 2022
Oh, what could've been... / Anadolu Agency/GettyImages

Recency bias is undoubtedly playing a role here, but England's most recent World Cup defeat is one of the most painful for many reasons.

They were equal to if not superior to France in their quarter-final matchup and had the chance to draw level after Olivier Giroud had given the holders their second lead of the match when Theo Hernandez bundled Mason Mount over in the box.

The so-often-emphatic-from-12-yards (as he proved 30 minutes earlier) Harry Kane stepped up but blazed his spot kick into orbit. A nation wept.

This is such a likeable England squad and their performances in Qatar suggested they were capable of finally bringing football home. You would have backed them against any team left in the tournament had they beaten Les Bleus and advanced into the last four.

1. Semi-final vs West Germany (Italia '90)

Paul Gascoigne, Lothar Matthaus
Lothar Matthaus consoles Paul Gascoigne after England's semi-final defeat at Italia '90 / Getty Images/GettyImages

Much of the noise surrounding England heading into Italia '90 focused on their supporters as opposed to Bobby Robson's team which endured a miserable Euro '88 campaign.

Expectations were low as a result with the media back home ready to stick the knife in Robson after an abject draw against Ireland on Matchday 1.

Slowly but surely, however, Robson's Three Lions began to get the country to believe. An impressive performance in a stalemate with the Dutch helped turn the tide as they progressed into the knockouts following a slender win over Egypt.

Hard-fought triumphs over Belgium and Cameroon then lifted England into their first World Cup semi-final since 1966 where their most bitter rivals awaited. West Germany were the cream of the crop and favourites to go all the way, but England produced an admirable display which should've culminated in victory.

If only Chris Waddle's effort in extra time had nestled in the bottom corner...

Penalties ensued but the Germans were perfect. England were not. Stuart Pearce had his effort saved before Waddle infamously blazed over. While the defeat encapsulated heartbreak like no other in English football history, Robson's side had won over the hearts and minds of naysayers back home.