Jakub Błaszczykowski missed the crucial penalty as Portugal beat Poland from the spot.
The former Fiorentina winger missed the only penalty of the shoot-out after the sides couldn’t be separated at 1-1 after normal time and extra-time.
The Poles had only conceded one goal in their four games up to this point, but had worries over star man Robert Lewandowski, who had yet to hit the back of the net.
That all changed with less than two minutes on the clock. Kamil Grosicki picked the ball up on the left flank and cut a perfect ball back for the Bayern Munich striker.
It was by no means an easy finish, but Lewandowski took it first time to fire it into the corner of Rui Patricio’s goal.
The striker could have made it two, spinning round Pepe on the edge of the box before driving his shot at Patricio from a difficult angle.
Portugal were struggling to get their own star man, Cristiano Ronaldo, into the game, but Łukasz Piszczek presented him with a chance.
The right-back was slow on the ball, and Nani stole in to lay it off to the Real Madrid man, whose low shot was saved by Łukasz Fabianski.
That was Portugal’s first shot on target, but their second brought the equaliser. Renato Sanches cut inside, played a one-two with Nani and his left-footed strike took a deflection which beat Fabianski.
After the break, Ronaldo could have squared for Joao Mario but took the shot on himself and hit the side netting.
Nani found Ronaldo, but his miscued his shot and it ended up behind him.
The game became a lot more cagey, but Milik tested Patricio with a volley and Jose Fonte headed straight at Fabianski from a corner.
With ten minutes remaining, Artur Jędrzejczyk breathed a sigh of relief, as his interception saw the ball ricochet off his shin and go just wide of his own goal.
Ronaldo could have won the match for his country on 85 minutes. Substitute Joao Moutinho’s chipped pass found him in the area, but with the goal at his mercy he failed to connect with a left-footed volley.
The Real Madrid man had another chance in the opening minute of extra-time, but he couldn't connect properly with Eliseu’s cross.
That sent the match to penalties, with Ronaldo and Lewandowski going first and scoring for their respective countries.
The standard of spot-kick was high, with every player scoring until Rui Patricio dived to his left to save Błaszczykowski’s effort.
That put the match at Ricardo Quaresma’s feet, and the former Inter man made no mistake to send Portugal through, the only side to reach the Semi-Final without winning a match in normal time.
Poland 1-1 Portugal [Portugal win 5-4 on pens]
Poland: Fabianski; Piszczek, Glik, Pazdan, Jędrzejczyk; Błaszczykowski, Krychowiak, Mączýnski (Jodłowiec, 98), Grosicki (Kapustka, 82); Milik, Lewandowski
Portugal: Rui Patricio; Cedric, Fonte, Pepe, Eliseu; W. Carvalho (Danilo, 96), Adrien (Moutinho, 73), Joao Mario (Quaresma, 80), Renato Sanches; Nani, Ronaldo
Referee: Felix Brych [GER]