A laborious 90 minutes was followed by a semi-exciting extra-time, but neither Cristiano Ronaldo nor Alexis Sanchez could prevent the fixture from ending 0-0.
And so it was left to penalties to decide the tie.
Typically of Ronaldo, the Portuguese wanted to be one of the last players to take a penalty and so left himself out of the first three.
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Ronaldo puts a comforting hand on Quaresma's head
Unfortunately for the Real Madrid striker, three successful Chile spot kicks and three Claudio Bravo saves meant he never got the chance.
But if you thought the four-time Ballon d'Or winner might kick off or throw a strop, you'd be wrong.
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Captain perfect: Ronaldo is a team player
Footage has emerged of the Portugal captain instead doing something amazing. After Ricardo Quaresma and Joao Moutinho missed their efforts, Ronaldo consoled them on the halfway line, separately and together.
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Cristiano Ronaldo consoles Joao Moutinho
When Nani had his penalty saved, the 32-year-old forward rallied his troops together and led them off the pitch.
Brave in the face of defeat, Ronaldo then went to congratulate Bravo on his shootout heroics.
Despite Fernando Santos's men still having the third/fourth play-off against Mexico on Sunday, the 32-year-old forward has been allowed to fly home after the birth of his twins.
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