Olivier Giroud's first-half strike proved the difference as Milan battled through to the Champions League last four with a 1-1 draw at Napoli to secure a 2-1 aggregate triumph.
Ismael Bennacer's goal last week at San Siro snatched a 1-0 quarter-final lead and Milan deservedly doubled their aggregate advantage in the first half on Tuesday in Naples.
Giroud had an earlier penalty saved by Alex Meret but made amends soon after with his 43rd-minute opener after Rafael Leao's incredible run to create the goal.
Victor Osimhen's stoppage-time strike offered Napoli hope after Khvicha Kvaratskhelia's 82nd-minute penalty was saved by Mike Maignan, but Milan held on to reach their first Champions League semi-final since 2007.
Matteo Politano twice whistled early efforts narrowly wide but the Rossoneri should have struck first when a clumsy Mario Rui lunge on Leao offered Milan a glorious chance from 12 yards.
Yet Meret guessed the right way to deny Giroud's spot-kick towards the bottom-right corner, before again thwarting the France veteran after another tame effort from a gilt-edged opportunity.
The Milan striker made no mistake next time round as Leao showed a remarkable turn of pace down the left before rolling across to Giroud for the simplest of tap-ins.
Victor Osimhen saw a strike ruled out for handball on the stroke of half-time and Kvaratskhelia blasted just over after the interval as Napoli searched for a response.
A Fikayo Tomori handball afforded Napoli a late opportunity to fight back into the clash, though Maignan dived low to his right to thwart Kvaratskhelia.
That penalty miss proved Osimhen's late header from Giacomo Raspadori's cross in vain as Milan battled through to the last four.
What does it mean? Milan frustrate Napoli once more
Runaway Serie A leaders Napoli have been by far and away the dominant force in Italy this season, yet Milan have had the edge over Luciano Spalletti's side.
The Rossoneri defeated Napoli twice in April, yet this draw will likely serve as the most punishing blow after Spalletti's men were sent crashing out of Europe in front of their vociferous home supporters.
A potential semi-final meeting with city rivals Inter awaits for Milan if the Nerazzurri can overcome Benfica in Wednesday's second leg. Simone Inzaghi's side lead the tie 2-0.
Giroud emulating fellow veteran Ibrahimovic
Giroud became the first Milan player to see a Champions League penalty saved since the 2005 final when Liverpool's Jerzy Dudek denied Andriy Shevchenko in the shootout, yet the France striker responded well.
The Milan striker's strike took him onto seven goal involvements in 10 European outings this term, only Zlatan Ibrahimovic has managed more for the Rossoneri in a single Champions League campaign (nine in 2011-12).
Not so super Mario
Rui had a game to forget after needlessly giving away the first-half penalty for an unnecessary and ill-timed lunge on Leao.
The left-back was fortunate to see his blushes spared by Meret but was forced off injured after just 34 minutes, having already lost possession a team-high nine times in a poor showing.
What's next?
Napoli return to Serie A action at Juventus on Sunday, when Milan host Lecce.
Sporting CP boss Amorim apologises for holding West Ham talks
Sporting CP coach Ruben Amorim has publicly apologised for holding talks with West Ham, who view the 39-year-old as a contender to replace David Moyes at the end of the season.
This week, widespread reports said Amorim had travelled to London for talks with the West Ham hierarchy, as they weigh up their options ahead of Moyes' contract expiring in June.
Moyes delivered the Europa Conference League trophy to the London Stadium last season but has long struggled to win over sections of the Hammers' fanbase, and a poor run of form has seen their hopes of European qualification fade in recent weeks.
Amorim, who led Sporting to the Primeira Liga crown in 2020-21 and looks likely to oversee another title triumph this term, has also been linked with Chelsea and Liverpool in the past.
He was roundly criticised for making the trip to London while still under contract, and on Saturday he admitted the visit was a mistake.
"So, let's get the elephant out of the room and I'll talk about it once," Amorim said in a press conference to preview Sunday's trip to Porto.
"The first thing is to say that the club was aware of my trip. It's important and changes the context.
"Then, let's talk about the 'cloak of secrecy' that surrounded the trip... I 'secretly' parked the car outside, secretly walked past 15 people and took photographs, then got on a plane behind the club's back.
"It didn't happen in secret or without permission. Obviously my trip was a mistake, the timing was completely wrong, it didn't seem right at the time.
"It was wrong, especially when I'm so demanding with my players and always the first to say that each one's actions can overpower the team. I have removed players from the squad for much less.
"It was my mistake, I have to accept it and live with it. It didn't seem so bad at the time but thinking about it later, it's very clear.
"Now it's time to move on. I apologise to the Sporting fans, the staff and, mainly, to my players for the mistake I made."
Wilder laments "complete lack of leadership" as Blades' relegation confirmed
Chris Wilder feels his Sheffield United side's "complete lack of leadership" has been a key factor in their relegation from the Premier League.
The Blades will be playing Championship football next term after a dismal one-season return to the Premier League in which they have won just three of their 35 league outings.
Sheffield United's 25th league defeat of the season confirmed their relegation as they were hammered 5-1 away at Newcastle United on Saturday despite Anel Ahmedhodzic putting them in front at St James' Park.
A drubbing ensued after Alexander Isak's leveller, and the final whistle condemned the Blades to the second tier with three games to spare.
In Wilder's view, the club needs to rectify a lack of on-field guidance if the Blades are to bounce straight back up, embodied by the tough outing at St James' Park.
Wilder told the BBC's Match of the Day. "There are plenty of games where we have been put to bed early but today we should have been 3-0 up at half-time. I'm scratching my head that it was 1-1.
"Newcastle up their game and get a head of steam. Then our old mistakes start to fall in and goals go from two to three to four to five pretty quickly.
"There's a reason why that happens. It's an incredibly young side and there is a complete lack of leadership out there. I thought at times I was going to have a heart attack in terms of trying to get the messages on."
Wilder acknowledged there could be tough times ahead for the club, though he hopes he retains the trust of the fans having been brought in for his second spell as Blades manager midway through the season following the sacking of Paul Heckingbottom.
"It's going to be a tough summer for everybody," Wilder continued. "We have not been good enough. The league has been too powerful for us right the way through the season.
"Sheffield United is a really good football club. I think everyone understands that but it's been a really poor season.
"I've still got another year left of my contract. I'd like to think that the supporters can trust me. I'm enthusiastic and committed along with my coaching staff to get it right. We know exactly what direction we need to go, what the culture is going to look like, what pre-season is going to look like."
Huddersfield Town all but relegated from Championship while League Two play-off fate is decided
Huddersfield Town saw their relegation all but confirmed after a 1-1 draw with fellows strugglers Birmingham City.
The Terriers avoided a defeat that would have seen them relegated on Saturday, but even a win on the final day over promotion hopefuls Ipswich Town will not be enough unless they overcome a huge goal difference of 15 goals with Plymouth Argyle.
Birmingham remain in the other relegation place and now must beat Norwich City to stand a chance of staying up with Sheffield Wednesday, Plymouth and Blackburn Rovers also still in danger.
At the other end of the table, the Canaries dropped points in a 2-2 draw with Swansea City, leaving the door open for Hull City, who face Ipswich Town later today.
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