Ismael Bennacer scored the only goal of the game as Milan secured a slender Champions League quarter-final advantage over 10-man Napoli with a 1-0 win in Wednesday's first leg.
Just over a week after being thrashed 4-0 by Milan in Serie A, Napoli were the dominant force for large parts at San Siro – only for Bennacer to deal a sucker punch after 40 minutes.
The Algeria international's first Champions League goal proved the difference as Napoli, who had Frank Anguissa dismissed in the second half, were unable to respond without injured star striker Victor Osimhen.
Luciano Spalletti will hope to have Osimhen, and his replacement Giovanni Simeone, back fit for the return leg as Napoli bid to overturn a narrow deficit at home next Tuesday.
Rade Krunic's goal-line block denied Khvicha Kvaratskhelia with the goal gaping after his own errant pass teed up the Georgia winger with less than a minute on the clock.
Anguissa and Piotr Zielinksi both forced smart Mike Maignan saves soon after, before Rafael Leao wasted a glorious chance by dragging Milan's first opportunity wide.
Napoli did not heed that warning, though, as Brahim Diaz exchanged passes with Leao and flicked towards Bennacer, who smashed a left-footed strike past the helpless Alex Meret.
Milan should have doubled their lead on the stroke of half-time but Simon Kjaer headed against the crossbar from Theo Hernandez's corner.
Maignan tipped an Eljif Elmas header onto the crossbar after the interval, though Napoli's comeback hopes were halted with 16 minutes remaining when Anguissa was dismissed for two quickfire yellow cards.
Yet Milan still needed late heroics from Maignan, who parried wide from a late Giovanni Di Lorenzo header.
What does it mean? Advantage Milan after profligate Napoli showing
Earlier in the month, Milan handed Napoli their heaviest league defeat since December 2007 and their biggest margin of defeat in a home Serie A game since October 2000.
The Rossoneri's showing here was far less rampant and much more industrious, scoring with their first shot on target after Napoli had nine attempts – three of those testing Maignan – inside the opening 23 minutes.
Milan may not be able to rely on such fortune in the return leg, albeit they will head to Naples with a remarkable record – having lost just one of 10 all-Italian match-ups in Europe (W5 D4).
Brilliant Brahim
Brahim's genius was the key to unlocking the Napoli defence in the first half, spinning to take two players out the game before teeing up Bennacer from Leao's return pass.
That continued Brahim's strong form against Napoli with his third goal involvement when facing the Partenopei – his joint-most against an opponent in all competitions (along with Torino).
Rossoneri rumble Napoli defence again
Napoli have been the dominant force in Italy, and tipped as a European favourite by many, but the Partenopei have been unable to get to grips with Milan's attack this term.
Spalletti's side have conceded six times against Milan in all competitions this campaign, twice as many as they have against any other side (Cremonese, Ajax and Liverpool – all three).
What's next?
Before the return meeting at the Diego Armando Maradona Stadium, Napoli host Verona in Serie A on Saturday – three hours after Milan kick off at Bologna.
Hurtig the hero after late goal sends Arsenal into Champions League quarters
Lina Hurtig's 89th minute winner ensured Arsenal progressed to the quarter-finals of the Women's Champions League after edging Juventus 1-0 on Thursday.
After being frustrated for large parts of the encounter, Hurtig bundled home from close range after Martina Lenzini's poor clearance to book the Gunners' place in the last eight.
Despite Arsenal dominating the early exchanges, it was Juventus who had the first sight of goal, though Eva Schatzer's effort was easy for Daphne van Domselaar to gather.
In a first half that saw just two shots on target, both coming from the visitors, Renee Slegers' substitutes proved to be the difference for Arsenal.
Slegers introduced Beth Mead, Stina Blackstenius and Hurtig late on, with the latter somehow putting Kim Little's cross over the bar from five yards out.
However, the Swede would atone for her earlier error, combining with fellow substitute Blackstenius to net against her former club and send them out of the competition with two group games remaining.
Meanwhile, in Group D, Barcelona edged closer to the quarter-finals of the competition with a convincing 4-1 victory over St. Polten at the Generali Arena.
The reigning champions are still three points behind Manchester City following their 2-1 win over Hammarby, and know a win against the Swedes next month will see them progress.
Kika Nazareth opened the scoring in the 20th minute after capitalising on a mistake by Kamila Dubcova, notching her second nine minutes later from close range.
Barca found themselves three goals up at the break when Vicky Lopez netted her first goal in the competition to put the result beyond doubt.
There was also a landmark moment for Alexia Putellas, who netted her 200th goal for the club with a well-taken effort into the far corner.
Valentina Madl took some of the shine off an otherwise impressive display from the visitors, who have now taken their tally to 20 goals from their four matches in the competition.
Guardiola agrees two-year contract extension with Man City
Pep Guardiola will be Manchester City manager for at least two more seasons after 2024-25, after he signed a two-year contract extension on Thursday.
The 53-year-old was coming to the end of his City deal, which was due to expire at the end of the current campaign, but he has opted to remain at the Etihad Stadium.
The deal itself will take Guardiola's tenure at the club to over a decade, making him City's longest-serving manager since Les McDowall in 1963.
There had been suggestions that he may leave at the end of the season following the announcement that director of football Txiki Begiristain was on his way out.
Guardiola was strongly linked with the England job after Gareth Southgate resigned in the wake of their Euro 2024 final defeat, but the Football Association appointed Thomas Tuchel last month.
“Manchester City means so much to me," Guardiola said. “This is my ninth season here; we have experienced so many amazing times together. I have a really special feeling for this football club.
“That is why I am so happy to be staying for another two more seasons.
“Thank you to everyone for continuing to trust and support me – The Owner, The Chairman Khaldoon, Ferran, Txiki, the players and, of course, the fans… everyone connected to Manchester City. It has always been an honour, a pleasure and a privilege to be here.
“I have said this many times before, but I have everything a manager could ever wish for, and I appreciate that so much.
“Hopefully, now we can add more trophies to the ones we have already won. That will be my focus.”
Having been appointed in 2016, Guardiola is by some distance Manchester City's most successful manager of all time, having won 18 major trophies during his time at the club.
That list includes their first-ever Champions League triumph in 2023 and six Premier League titles, including an unprecedented four on the spin.
He also boasts a 72.04% win percentage across all competitions, which is unsurprisingly the highest of any full-time City manager in history.
Shaw at the double as Man City progress in Champions League
Khadija Shaw scored twice as Manchester City beat Hammarby 2-1 to seal their place in the Women's Champions League quarter-finals.
Gareth Taylor's team entered Thursday's game with a perfect record in Group D, and their fourth win in as many European matches ensured they finished in the top two.
Shaw—the leading scorer in the Women's Super League this season with eight goals—put them ahead in the 31st minute, driving into the area after taking in Yui Hasegawa's pass before seeing her shot deflect into the top corner.
Shaw was booked for celebrating in front of the home fans despite appearing to have objects thrown at her from the stands, and Hammarby should have levelled when Julia Blakstad fired wide 10 minutes later.
The hosts did draw level three minutes into the second half as Ellen Wangerheim tapped home while City's Laura Blindkilde Brown was down appealing for a free-kick.
That parity was short-lived, though, as Shaw blasted into the top corner from 25 yards out, taking her overall tally for this season to 12 goals in all competitions.
In Group C, meanwhile, Bayern Munich lost their perfect record as they played out a 1-1 draw with Valerenga, boosting Arsenal's hopes of topping the pile.
Jovana Damnjanovic came off the bench to put Bayern ahead 15 minutes from time in Norway, but Elise Thorsnes headed home following an 88th-minute corner to snatch a point for the hosts.
Arsenal could now move within a point of Bayern when they face Juventus in Group C's other match later on Thursday.
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