In the end it wasn't to be. And in a cruel twist of fate, it was penalties again which did for Gareth Southgate.
Twenty-five years ago it was Southgate himself who was the fall guy as England bowed out to Germany in the semi-final of Euro '96.
And at Euro 2020, Southgate could only watch from the sidelines as Marcus Rashford, Jadon Sancho and Bukayo Saka all missed from the spot to hand Italy the Henri Delaunay trophy.
It was a sad conclusion to what has been a hugely uplifting tournament for Southgate and his men.
Not that there haven't been plenty of iconic moments from his time in charge of England to look back on...
Leading England Under-21s
Southgate was appointed Middlesbrough manager in 2006 after retiring from playing for the club and was thrown straight in at the deep end. A disappointing three years at the Riverside saw him take a hiatus from coaching, before returning with England U-21s in 2013. He then led the team to the 2015 U-21 European Championships, but they could only finish bottom of their group.
There was better to come at the 2016 Toulon Tournament, though. Goals from Chelsea duo Lewis Baker and Ruben Loftus-Cheek gave England a 2-1 victory over France to lift the trophy.
That would prove to be Southgate's last tournament in charge of the under-21s - as a much bigger job awaited.
Landing the England job
After Roy Hodgson's departure following a disappointing Euro 2016 campaign, Southgate initially stated that he had no interest in replacing the veteran boss.
The job instead went to Sam Allardyce, who left the post after just one game (he still boasts the best win percentage of any England manager with 100%).
Southgate was put in temporary charge and some solid, if unspectacular, results came under his leadership. Nevertheless, they were enough to earn him the job on a permanent basis and he signed a four-year deal that would see him through the 2018 World Cup and Euro 2020.
Southgate was under little pressure heading into his first major tournament and maybe that was a good thing, because his England team fared far better than most people were expecting.
The 2018 World Cup
Southgate had gone to Russia having been told by the FA that even if England failed to make it out of the group stage, his job would still be safe.
However, it became clear very early on that his team would progress beyond that point. A 6-1 blitz of Panama was the highlight of the group stage, before a round-of-16 penalty shootout win over Colombia ignited hopes of World Cup glory for Southgate's men.
Sweden were dispatched comfortably in the quarter-finals before England came unstuck against Croatia in the semi-final despite having taken an early lead. It was a tough defeat to take, having come so close to the final.
Nevertheless, Southgate and his players had done themselves proud at an international tournament for the first time in years.
Southgate's chosen attire for the World Cup was a stylish yet unassuming waistcoat that grew in popularity as the tournament progressed.
Some retailers saw their waistcoat sales rise by 35% and #WaistcoatWednesday became a trend on Twitter to celebrate his fashion choice. Southgate tube station was temporarily renamed 'Gareth Southgate' in honour of what his side had achieved in Russia.
Qualifying for the 2019 Nations League finals
Just four months after the World Cup, Southgate and England found themselves on the verge of qualifying for another tournament. This time it was the first ever Nations League and a familiar opponent stood in their way - Croatia.
It may not have been a World Cup semi-final, but coming from a goal down to beat Croatia and secure a spot in the Nations League finals was as close to revenge as England were going to get.
The tournament itself was forgettable, with an extra-time loss to the Netherlands in the semi-final ending England's hopes. However, a penalty shootout win over Switzerland did earn Southgate's men third place.
Being unafraid to cap young players
One of the relatively unique things about Southgate's reign as England boss is the number of debuts he has given to young players.
Mason Mount, Phil Foden, Bukayo Saka and Jude Bellingham are just some of the names to have played under Southgate's new look England while the likes of Wayne Rooney and Joe Hart, despite their wealth of experience, have been ruthlessly left out of the squad.
It seems to have worked with back-to-back major tournament semi-finals, including narrowly being defeated in the final of Euro 2020 to Italy.
Southgate has three individual awards to his name, all for his superb work at the 2018 World Cup.
First, he was the recipient of the BBC Sports Personality of the Year Coach Award in 2018. A year later, he won the Football Writers Association Tribute award 2019 for helping reconnect the national team to their fans and the media.
He was also honoured by the Queen, being included on the 2019 New Years Honours List and receiving an Order of the British Empire (OBE) for services to soccer.