England's men have now gone 58 years since their last success in a major tournament, when they lifted the 1966 World Cup on home soil.

They came close to ending the run at Euro 2020 but ultimately lost to Italy on penalties in the final, and the period between those days has been filled with plenty of disappointment.

BBC Sport has picked 10 of the most heartbreaking moments including penalty shootout exits, red cards and shock defeats.

We've only picked out moments from tournaments themselves, not times when England have failed to qualify - those are too painful to even mention!

Let's start with arguably the most painful of them all.

England played five of their group and knockout stage matches at Wembley as they reached the final and football fever swept the nation.

Luke Shaw's early goal gave them the perfect start against Italy but they were pegged back by Leonardo Bonucci.

They went on to lose 3-2 on penalties with substitutes Marcus Rashford, Jadon Sancho and Bukayo Saka failing to score. It had to be penalties, didn't it?

The tournament that started to reignite belief.

England made it to the semi-finals and took the lead against Croatia with an early Kieran Trippier free-kick, but they eventually lost in extra time. A defeat by Belgium in the third-placed play-off followed too.

There was one positive from the tournament though: England ended a run of five straight defeats in penalty shootouts with success over Colombia in the last 16.

One of the most disappointing exits.

England were heavy favourites against Iceland and led within five minutes through Wayne Rooney.

But less than a quarter of an hour later England were behind and they were unable to turn it around, leaving Roy Hodgson rubbing his face in disbelief in the dugout and later without a job.

It feels odd to call a 4-1 thrashing a controversial exit but that is exactly what England's defeat by Germany in the last 16 was.

Fabio Capello's side had stuttered through the group stage and went 2-0 down to the Germans before Matthew Upson got one back.

Frank Lampard - and the whole England team - thought they had levelled with a superb dipping strike that bounced off the bar and clearly crossed the line but Uruguayan referee Jorge Larrionda and his officials waved play on.

England were incensed at the break and conceded two second-half goals to be knocked out.

England were far from fluent at the 2006 World Cup - needing an own goal to beat Paraguay, before two late goals saw them past Trinidad and Tobago to secure progression.

A 1-0 win over Ecuador thanks to David Beckham's goal put them in the quarter-finals but another tight affair lay ahead.

Wayne Rooney was sent off in the last-eight tie against Portugal, and there was the famous wink from Manchester United team-mate Cristiano Ronaldo after the incident too.

England held on for a goalless draw after extra time but lost 3-1 on penalties with only Owen Hargreaves scoring.

We're starting to get a bit of a theme now, aren't we?

Penalties, Portugal and key players being involved in moments to forget on the way to another exit.

England led early in this quarter-final through Michael Owen before Rooney was forced off through injury in the first half.

The Three Lions were pegged back late on by Helder Postiga, before Rui Costa and Lampard scored in extra time to force penalties.

England went on to lose 6-5 with David Beckham blazing the first spot-kick high and wide, while Darius Vassell saw his effort saved.

Knockout games are hard to win at the best of times, but a red card really does damage your chances.

England actually led in the last-16 tie as Alan Shearer and Michael Owen cancelled out Gabriel Batistuta's opener for Argentina.

Javier Zanetti equalised in first-half stoppage time before Beckham was sent off two minutes into the second half for kicking out at Diego Simeone.

England lost the shootout 4-3 with Paul Ince and David Batty both missing.

Beckham, of course, went on to score the winner against Argentina in the 2002 World Cup.

England got past Spain in the quarter-finals with a 4-2 penalty shootout win, following a 0-0 draw.

Their success from the spot was never going to continue though, was it?

They lost 6-5 to Germany in the semi-finals, following a 1-1 draw after extra time, with current manager Gareth Southgate seeing the decisive penalty saved.

You guessed it, more penalty pain.

It was at the hands of West Germany this time and came after a 1-1 draw with Gary Lineker cancelling out Andreas Brehme's opener in the semi-final.

England lost 4-3 on penalties with Stuart Pearce and Chris Waddle failing to score.

Paul Gascoigne was in tears after the game and that image has become one of the most memorable in England's football history.

Another controversial exit thanks to Diego Maradona's famous 'Hand of God' goal for Argentina.

Maradona rose above Peter Shilton and flicked the ball in with his hand to give Argentina the lead in their quarter-final.

Referee Ali Ben Nasser from Tunisia awarded the goal and then sought confirmation from his linesman after England protested.

Maradona scored again four minutes later before Lineker pulled one back late on.

Shilton said in 2020 that Maradona never apologised for the goal and it had "left a bitter taste".