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England's new generation ended the World Cup penalty jinx by knocking out Colombia on spot-kicks to reach the quarter-finals.
Eric Dier scored the winning kick after Jordan Pickford's brilliant save from Carlos Bacca's attempt, with England's first ever World Cup shootout win setting up a meeting with Sweden in Samara on Saturday, a game that can be seen live across the BBC.
Gareth Southgate's side had been seconds away from the last eight during normal time, with Harry Kane's penalty after he was fouled by Carlos Sanchez in the box - his sixth goal of the tournament - looking as though it was going to send them through.
But deep into injury time, Colombia threw everyone forward for a Juan Cuadrado corner, including goalkeeper David Ospina, and Yerry Mina headed a dramatic equaliser at the Spartak Stadium.
Kieran Trippier was standing on the line but could not keep out the Barcelona centre-back's third headed goal of the World Cup.
The Three Lions had been on top for most of the 90 minutes but appeared understandably deflated in extra time - although Danny Rose and Dier missed late chances to win the game and avoid a shootout.
Henderson had a penalty saved by Ospina in the shootout but Mateus Uribe smashed the following kick on to the crossbar to pave the way for Pickford and Dier to be England heroes.
No previous world champions stand between England and the final. The winners of their quarter-final will face either Croatia or hosts Russia for a place in Moscow on 15 July.
The game itself had been a bad-tempered affair, with eight players booked in total - six of them Colombians, including Wilmar Barrios, who was lucky to avoid red for a first-half headbutt on Henderson.
England survive test of nervePickford saves, Dier scores - England win penalty shootout
England's survived a test of nerve that will prove invaluable as they drive deeper into this World Cup after a night of noise, colour and hostility in Moscow.
Southgate's side cast off the clouds of dread that have come over England in penalty shootouts in the past, a psychological lift that may yet help them further down the line.
Colombia made their intentions clear from the off. This was going to be a scrap and Jose Pekerman's side would be the beneficiaries if England were dragged into it.
England lived on the edge in those physical exchanges but the manner in which they survived and came through that test will add an extra layer to the satisfaction.
And within the dogged team performance, individuals once more made their mark.
Everton goalkeeper Pickford received some criticism for his performance against Belgium but was outstanding here, not only saving that Bacca penalty but producing one of the saves of the World Cup from Uribe's thunderous drive from 30 yards - which cruelly led to the corner that brought Mina's equaliser.
And Trippier's measured penalty was another indication of his growing maturity at this level, the Spurs full-back having again performed solidly down England's right.World Cup 2018: England's historic penalty shootout win against Colombia in full
England edge towards glory
Southgate's one-match-at-time mantra has been designed to keep expectations in check as his side have been presented with their best opportunity at a World Cup since they reached the semi-finals of Italia 90.
If he was listening to the England fans who gathered and sang non-stop late into the Moscow night behind the goal in the Spartak Stadium, it may have dawned on him that keeping a lid on expectations is likely to be a losing battle.
England will have taken a lot out of themselves in this physically gruelling and mentally taxing last-16 game and they now face the well-organised and resilient Swedes.
If they can overcome Sweden, the possibility of a semi-final meeting with Russia or Croatia comes into view.
England found a way to win here that has often eluded them, digging deep in the process - and they will have headed back to their Zelenogorsk training HQ in soaring spirits.
There is work to do, though, and this was not a flawless performance by any means. But England and Southgate now have power to add to the momentum they have regained following the loss to Belgium at this spectacular Russian World Cup.
Referee Geiger lost the plot
American referee Mike Geiger's failure to clamp down on early misdemeanours led to him losing control of a game that Colombia seemed determined to turn into a battle.
Instead of imposing his authority on proceedings with firm decision-making, he instead indulged in lengthy discussion with players from both sides on numerous occasions.
It lead to Colombia, in particular, pushing him to the edge - although England were not total innocents, with both Henderson and Harry Maguire leaving themselves open to accusations of being over-theatrical and many others sailing close to the wind.
This would have been a tough night for any referee, with players clearly failing to respect his decisions, and making no attempt to make the official's life easier, but it is to be hoped officials with a greater sense of authority are handed the huge games that remain here in Russia.
Match stats - Kane sets best England run since 1939
- England have won a penalty shootout at a major tournament for only the second time, also beating Spain in Euro 96.
- England have qualified for the quarter-final of a World Cup for the first time since 2006.
- Colombia have lost three of their four knockout matches at the World Cup (also the last 16 in 1990 and the quarter-final in 2014).
- The team going first in a penalty shootout have now lost all three at the 2018 World Cup.
- Harry Kane became the first player to score in six consecutive England appearances since Tommy Lawton did so in 1939.
- Kane has scored six goals in his first three World Cup appearances for England - only three players have scored more in their first three matches; Hungary's Sandor Kocsis (nine), Germany's Gerd Muller (seven) and Argentina's Guillermo Stabile (seven).
- The last England player to be fouled more often in a World Cup match than Kane in this match (nine) was Alan Shearer in 1998 against Tunisia (11).
- Kane has scored 14 goals in 10 England appearances under Gareth Southgate, scoring in all eight matches he has played as captain (12 goals).
- Mina has scored in all three of his appearances at the World Cup, with all three headers.
- Kane has scored six goals from six shots on target at the 2018 World Cup.
- England conceded in injury time at the end of the second half for the first time in World Cup history, with Mina's goal coming after 92 minutes and 33 seconds.
- Eight of England's last 15 World Cup knockout matches have gone to extra time, with the first match in this run the 1966 World Cup final.