Olivier Giroud missed a penalty then scored the crucial goal to send AC Milan into their first Champions League semi-final for 16 years, by beating Napoli 2-1 on aggregate.
Milan arrived in southern Italy with a one-goal advantage and thought they had missed their best chance to double that lead when Giroud’s spot-kick was saved by Alex Meret just after the hour-mark.
But minutes before the break, Rafael Leao went on a superb solo run from the edge of his own box to the penalty area, before squaring to Giroud to tap home a simple finish.
Napoli, who welcomed back Victor Osimhen from injury in time for this game, also saw a penalty for themselves saved as Mike Maignan denied Khvicha Kvaratskhelia with 10 minutes to go, before Osimhen headed in a late consolation.
Milan will now turn their attentions to a potential semi-final against city rivals Inter, who are 2-0 up ahead of their home Champions League quarter-final second leg with Benfica on Wednesday night.
A cauldron of noise welcomed the Stadio Diego Armando Maradona at kick-off and blue smoke ran through the air as the game got underway.
Napoli used that support to make a fast start. Kvaratskhelia and Piotr Zielinski saw routine shots saved by Maignan, while Matteo Politano saw two near-post efforts flash wide of the AC Milan goal.
The Rossoneri’s defence remained firm and Stefano Pioli’s side were given a brilliant chance to get their first goal of the night as Leao went down under Mario Rui’s clumsy challenge to earn a penalty.
Giroud stepped up but Meret guessed right – to produce more noise amongst the Napoli supporters.
Luciano Spaletti’s side were then given a double injury blow as Rui and Politano were forced off in the space of two minutes with knocks, as Hirving Lozano and Mathias Olivera came on.
Milan nearly took advantage of the readjustment as Giroud saw a close-range effort well saved by Meret – but the Napoli goalkeeper would not be denied just minutes before the half-time whistle.
Leao picked up Tanguy Ndombele’s clumsy touch near the edge of his own area and beat three flying Milan challenges en route to the penalty area.
The Portuguese international then had the unselfish awareness to square to Giroud, who could not miss that chance.
Napoli hotshot Osimhen nearly had an immediate response to the ‘Giroud Show’ when he fired in from close range in first-half stoppage time, but the goal was ruled out for a handball by the Serie A top scorer in the build-up.
Napoli’s Mario Rui (right) was one of two first-half casulaties
The hosts came out with a similar endeavour after the break as Kvaratskhelia blazed over two chances from the left in the opening minutes of the second half.
In a second period which saw Napoli dominate proceedings but fail to land a blow on a superb Milan defence, Lozano, Olivera and Amir Rrahmani all had good opportunities to pull one back but all failed to succeed.
Napoli thought they were about to get in the game on 82 minutes when Elfir Elmas’ cross hit Fikayo Tomori on the hand and the referee pointed to the spot.
But Kvaratskhelia’s spot-kick was smartly stopped by Maignan in Napoli’s final wasteful moment of the evening.
Maignan would go on to save from Giacomo Raspadori from close range to further frustrate Napoli. And despite Osimhen heading past the Milan goalkeeper two minutes from time, it is now just an inevitable Serie A title left to seal for the league leaders.
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