Penalty pain and Wembley joy – A look at England’s past semi-final showdowns

England are one game away from a place in the final of Euro 2024.

Composite image of Gareth Southgate being consoled by David Seaman and Declan Rice celebrating with Jordan Henderson

England take on the Netherlands on Wednesday looking to reach a second successive European Championship final.

It will be the sixth time England have played in the semi-finals of a major tournament, not including the 1968 European Championship when only four teams qualified for the finals.

Here, the PA news agency takes a look at how England got on in their previous last-four encounters.

England 2 Portugal 1 – 1966 World Cup

England came through against a Portugal side including Eusebio in 1966 (PA)

Portugal had a 100 per cent record going into the match at Wembley and seven of their 14 goals came from an inspired Eusebio. However, Bobby Charlton struck in either half which meant that, while Eusebio inevitably pulled one back from the penalty spot late on, it was ultimately a mere consolation. The rest, as they say, is history.

West Germany 1 England 1 (West Germany won 4-3 on penalties) – 1990 World Cup

Gazza’s tears and the start of their penalty shootout woes were the legacies of England’s biggest game since seeing off the same opponents in the final 24 years earlier. Gary Lineker cancelled out Andreas Brehme’s deflected effort at the Stadio delle Alpi before, in the shootout, Stuart Pearce saw his spot-kick saved and Chris Waddle blazed over.

Germany 1 England 1 (Germany won 6-5 on penalties) – 1996 European Championship

Gareth Southgate's missed penalty led to England being knocked out of Euro 96 (PA) — Gareth Southgate’s missed penalty led to England being knocked out of Euro 96 (PA)

A familiar opponent and outcome as 30 years of hurt continued at Wembley. Alan Shearer headed England in front early on, but Stefan Kuntz soon levelled and, while Paul Gascoigne was agonisingly close to sliding in a winner in extra-time, the teams could not be separated after 120 minutes. Remarkably, the first 10 penalties were scored in the shootout, meaning Gareth Southgate’s miss proved decisive.

Croatia 2-1 England (after extra time) – 2018 World Cup

England were left disappointed after going out to Croatia after extra time in 2018 (Adam Davy/PA)

Now the manager, Southgate led England back to the sharp end of a major event once more but, despite Kieran Trippier’s early free-kick giving them reason to believe, Croatia had other ideas. Ivan Perisic struck midway through the second half at Moscow’s Luzhniki Stadium before Mario Mandzukic struck in extra time to break English hearts.

England 2 Denmark 1 (after extra time) – 2020 European Championship

Harry Kane, right, lifted England into the Euro 2020 final (Mike Egerton/PA)

Falling behind to Mikkel Damsgaard’s goal might have invoked a familiar sinking feeling within England fans, but Simon Kjaer’s own goal sent the match to an additional 30 minutes at Wembley. A nerve-wracking shootout was avoided when Harry Kane converted after his penalty was saved as England ended their semi-final hoodoo. However, more penalty heartbreak awaited England in the final against Italy.