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.
Rangers 1-4 Lyon: Lacazette and Fofana at the double as Clement's men outclassed
Malick Fofana and Alexandre Lacazette each scored twice as Lyon outclassed Rangers 4-1 in the Europa League at Ibrox on Thursday.
Former Arsenal striker Lacazette scored twice before the break after Tom Lawrence had earlier cancelled out Fofana's opener in Glasgow, with the latter also netting again in the second half.
Vaclav Cerny was punished for woefully blazing over the bar when Fofana bent home on the rebound from the hugely impressive Rayan Cherki's shot after 10 minutes.
Lawrence quickly prodded home the equaliser when Cyriel Dessers was denied, but an awful error from Connor Barron led to Fofana laying on a simple finish for Lacazette.
The Frenchman then made it 3-1 with a whipped 25-yard stunner before the break and Fofana poked home Cherki's low cross at the back post to add more gloss shortly after the restart.
Duje Caleta-Car saw a header thunder off the crossbar and Corentin Tolisso had a shot cleared off the line, while substitute Said Benrahma was also denied as Lyon pushed to really emphasise their dominance of proceedings.
Data Debrief: Lyon forwards tormentors in chief
Rangers, who won impressively at Malmo on MD1, just had no answer for the dynamism of a Lyon side who are now two from two and second in the table.
Lacazette was playing his 50th game in the Europa League and scored his 23rd and 24th goals in the competition. Only Pierre-Emerick Aubameyang (34) and Aritz Aduriz (26) have scored more since his first appearance in September 2012.
Cherki set up both of Fofana's goals in an excellent display and has six goal involvements in only five Europa League starts (three goals, three assists), while Fofana scored and assisted in the same game for the first time for Lyon.
Rangers have a night to forget and this represented only the first time in the Europa League/UEFA Cup they have conceded four goals at home, and only the third time overall.
City striker 'Bunny' Shaw targets more success with hopes of inspiring young girls in Jamaica
Despite achieving much of what she set out to already, Reggae Girl and Manchester City striker Khadija ‘Bunny’ Shaw intends to keep pushing the barriers and she hopes to inspire others to chase their dreams.
Shaw, who has overcome her fair share of obstacles and tragedies to get to where she is at, has been a role model for young athletes in Jamaica and the Caribbean, particularly aspiring women’s football players, as she continues to impress on the international stage and in the Women's Super League (WSL) since her move to City in 2021.
The 27-year-old ended last season as the WSL’s top scorer, assisting the Gareth Taylor-coached side to the runners-up position behind champions Chelsea, merely on goal difference.
Her performances throughout that campaign, which was cut short by a broken leg, also saw her cop the PFA Women's Players' Player of the year and the FWA Women's Footballer of the Year awards.
"When I look back at my childhood, I didn’t really have a lot of people I could look to, apart from Usain Bolt, of course. I didn’t have a lot of people who I could look to and say, ‘I want to be like that.’ One of the main reasons was that I wasn’t really allowed to play," Shaw said in an interview with BBC Sport.
“Now, looking at where the game is and where it is going, I think there is more room for that. For me, it’s just being alive and being in the moment. It’s staying true to who I am. Hopefully, by doing that each and every day, it works out in the end,” she added.
Black History Month in England, celebrated throughout the month of October, continues to shine a spotlight on athletes who have broken barriers to achieve success.
With her accolades and accomplishments speaking for themselves, Shaw is aiming to continue setting the standard for others to follow.
"I just try to be the best I can be and hope that by doing that, there are others looking on [who can] see that if I can do it, then it’s possible. Hopefully I can inspire a lot of the young girls back home in Jamaica that it is definitely possible,” the two-time Ballon d'Or award nominee shared.
"It’s been a long journey for me. I had to travel around the world to get here. Now I am here, I’m just embracing the moment and loving every part of it. The ups and downs are parts of life and that’s how you grow as a person. But I just try to be the best that I can and hopefully inspire more girls,” Shaw noted.
Chelsea 4-2 Gent: Veiga and Dewsbury-Hall off the mark in Conference League cracker
Renato Veiga and Kiernan Dewsbury-Hall each scored their first Chelsea goals in a cracking 4-2 victory over Gent in the Europa Conference League on Thursday.
Enzo Maresca decided to make wholesale changes in the Blues' opening match of the league phase of Europe's third-tier competition, but they were still a class above their Belgian opponents.
Full-back Veiga headed Chelsea into a 12th-minute lead after Mykhailo Mudryk stood up a brilliant cross from the right and Dewsbury-Hall fired into the side-netting when he ought to have scored soon after.
Despite their domination of the ball, it took the Blues until the 46th minute to double their lead when Pedro Neto took hold of Axel Disasi's long punt and fired into the roof of the goal.
Some slack Chelsea defending was punished when Tsuyoshi Watanabe headed in from the cross of Andri Gudjohnsen, son of Blues great Eidur.
Christopher Nkunku rifled home from just inside the area after Gent failed to clear their lines just after the hour and Dewsbury-Hall shot straight through the goalkeeper after Nkunku was tackled attempting to take a shot – with Omri Gandelman celebrating a late consolation for the visitors.
Data Debrief: Dewsbury-Hall stakes his Chelsea claim
This was a great chance for a few Chelsea players to stake their claim for more regular Premier League minutes and Dewsbury-Hall put in an industrious performance to do his chances no harm.
Signed from Leicester City in the last transfer window, the centre midfielder had four shots in total, three of which were in the box, and scored from his one big chance. He also had an impressive 91.2% pass accuracy.
Neto too had a very lively outing, creating five chances in total and finishing with a pass accuracy rate of 97%.
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