Previous villains Gareth Southgate, David Batty, David Beckham and Stuart Pierce have plenty of company as Frank Lampard, Steven Gerrard and Jamie Carragher all missed from the spot, only Bayern Munich's Owen Hargreaves converted his chance.
The game took a dramatic turn on 62 minutes when Argentinean referee Horacio Elizondo showed striker Wayne Rooney a red card for violent conduct after an altercation with Manchester United club mate Cristiano Ronaldo after he appeared to stamp on defender Ricardo Carvalho.
The moment of madness from the Mancunian forced an England reshuffle, seeing the withdrawl of midfielder Joe Cole for lanky striker Peter Crouch.
With the match then seemingly at Portugal's mercy Luiz Felipe Scolari’s side seemingly lost their way.
Ricardo gets it right again
They were forced into long range shots and the shift of Cristiano Ronaldo to lone striker simply didn’t have the required effect as he failed to have the same sort of impact he does on the flanks.
England had a real chance to win the match in the dying seconds of regulation time only to have defender John Terry’s chance go agonizingly close.
Neither team were able to create any clear chances in extra time, substitute Aaron Lennon had his shouts for a penalty waved away after 106 minutes after another trademark mazy run into the box, while a minute later Portugal's substitute striker Helder Postiga had the ball in the back of the net only for it to be waved away for offside.
From then the match always seemed destined to be settled by penalties.
Earlier, the two sides played a high tempo but goalless first half of football.
Possession was evenly shared throughout the first half, with England preferring a patient build up while Portugal opted for a high paced game plan around the wings.
Both keepers had only one real save to make, Ricardo saving a Wayne Rooney blast after eight minutes, while his Man United teammate Cristiano Ronaldo tested England’s Paul Robinson in an almost identical fashion with the same result just one minute later.
Unbelievable: Wayne Rooney sees
red against Portugal
England though return home knowing that penalties have again condemned them to an early exit from a major tournament.
The fact is that they have never won a penalty shoot out at a World Cup, however further post mortems may discover a midfield full of players who had scored plenty of goals at club level but were simply unable to produce the same for their country.
Portugal finally have the opportunity to go one step further than the side led by the great Eusebio back in 1966 when they last made a semi-final.
Scolari’s men will play either Brazil or France for a spot in the World Cup final after he orchestrated the downfall of England for the third consecutive time.