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.
Girona 4-1 Espanyol: Miovski bags double as hosts ride on first-half blitz
Bojan Miovski scored twice as Girona thrashed Espanyol 4-1 in LaLiga at Estadi Municipal de Montilivi on Saturday.
Bryan Gil and Ladislav Krejci were also on the scoresheet as the home side raced to a 4-0 lead inside the first half hour, with Javi Puado scoring the visiting side's only goal after the break.
After the match was halted because of a fan being taken ill in the crowd, Gil opened the scoring when he unleashed a stunning long-range strike into the bottom corner with four minutes on the clock.
Gil was behind the second goal for Michel's side too, as he capitalised on a defensive error and crossed to Miovski, who made it 2-0 in the 16th minute before the pair combined again for a third five minutes later.
Donny van de Beek's header from Yaser Asprilla's corner was pushed in by Krejci for Girona's fourth in the 27th minute.
Espanyol got a consolation goal 10 minutes into the second half when Puado hit a long-range strike that found the back of Paulo Gazzaniga's net.
Girona, last season's surprise package, climbed to fifth in LaLiga with 21 points, while Espanyol are 19th and in the relegation zone with 10 points.
Milan 0-0 Juventus: Bianconeri maintain unbeaten start after Rossoneri stalemate
Milan and Juventus shared the spoils following a dour goalless draw at San Siro.
The Bianconeri maintained their unbeaten start to the Serie A season, but missed the chance to go second behind leaders Inter after a game lacking in quality and chances.
With the likes of Dusan Vlahovic and Arkadiusz Milik out injured, Juventus began the game without a recognised striker, as Teun Koopmeiners and Weston McKennie led the line.
Koopmeiners hit the side-netting from a tight angle after 10 minutes, while Kenan Yildiz grazed the post following a fine individual run midway through the half.
Alvaro Morata had Milan's best chance at the other end, but the former Juventus striker could only head wide from Rafael Leao's free-kick.
Opportunities did not fall as freely in the second half either, and both teams left the field to a chorus of boos on the referee's final whistle.
Data Debrief: Stubborn Juve take clean sheet tally into double figures
Juve are the first team to register 10 clean sheets in their opening 13 matches of a Serie A season since Roma (also 10) in 2013-14.
The Bianconeri have also kept five clean sheets in their first six away league games in a campaign for only the fourth time, also achieving the feat in 1967-68, 2004-05, 2023-24.
Meanwhile, Thiago Motta is only the fifth Juventus manager to go unbeaten in his first 13 league matches in charge (won six, drawn seven), after Jesse Carver, Cestmir Vycpalek, Antonio Conte and Maurizio Sarri.
'I love where I am,' says Simeone after 700th game in charge of Atletico
Diego Simeone said he is "calm and at peace" at Atletico Madrid after his side edged Deportivo Alaves 2-1 in LaLiga in his 700th game in charge of the club.
Atletico went behind through a Jon Guridi penalty in the seventh minute, but Antoine Griezmann drew them level from the spot in the 76th minute.
The winner came via Alexander Sorloth in the 86th minute as Atletico moved four points behind leaders Barcelona.
Simeone, who has been in charge of Atletico since 2011, is the first coach to manage 700 matches with the same LaLiga club.
"I live in the present, we are having a good time, the boys are working very responsibly," Simeone told DAZN.
"I am calm and at peace. I love where I am and that's it."
He managed Atletico to LaLiga title triumphs in 2014 and 2021 and also helped Los Rojiblancos win two Europa League titles in 2012 and 2018.
The game against Alaves was Simeone's 492nd LaLiga match in charge, and the Argentine has also managed the third-most games with a single club in the Champions League (109), after Alex Ferguson with Manchester United and Arsene Wenger at Arsenal.
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