Juventus crashed out of the Champions League at the last-16 stage as a defiant, 10-man Porto side beat them on away goals after extra time to book their place in the quarter-finals.
Sergio Oliveira’s free-kick in extra time, his second goal of the night, proved crucial as the Portuguese side hung on despite Adrien Rabiot’s immediate response and a late onslaught from Juve.
Porto held a 2-1 lead from the first leg and travelled to Turin desperate for an away goal, meaning their opponents would need to score twice to force the extra period.
And they were gifted the opportunity after just 18 minutes when Merih Demiral clattered into the back of Mehdi Taremi as he tried to turn and shoot inside the box.
The referee pointed to the spot and up stepped Oliveira to send Wojciech Szczesny the wrong way for his 16th goal of the campaign.
Cristiano Ronaldo was at the heart of Juve’s leveller after the break, collecting a ball over the top of the Porto defence and laying it off for Federico Chiesa to curl into the far corner.
Porto were then reduced to 10 men after Taremi was given two yellow cards in the space of three minutes, the second of which was for kicking the ball away.
Chiesa hit the woodwork just moments later but he did make Juve’s numerical advantage count by heading Juan Cuadrado’s ball into the box past Agustin Marchesin for his second of the night.
The Serie A side thought they had won it in stoppage time as Alvaro Morata tucked the ball home, but the linesman’s flag was raised and replays showed him to be offside.
And Cuadrado then rattled the crossbar with a stunning effort just moments before the end of normal time.
Oliveira struck a free-kick under the wall in extra time and past Szczesny, with Ronaldo turning his back and the ball going through his legs before reaching the goalkeeper.
Rabiot responded almost immediately with a header but Juve couldn’t score again and crashed out in dramatic circumstances.
It means there will be no sixth Champions League crown for Ronaldo to add to his collection this season.
He won the first of his European Cups at Manchester United in 2008 and added a further four in five years between 2014 and 2018 at Real Madrid.
Juve hoped by signing the Portuguese superstar they would join the winners’ circle on the continent, but their wait for a first Champions League since 1996 goes on.