Udinese heaped more pressure on AC Milan boss Stefano Pioli with a 1-0 win at the San Siro for their first Serie A victory this season.
Roberto Pereyra’s penalty just after the hour proved decisive as the Rossoneri slumped to a second successive home defeat and saw their winless run extend to four matches in all competitions.
AC Milan now find themselves in a fight to stay in the top four heading towards the international break – with Pioli facing more questions on his future.
Udinese created an early opening when Jordan Zemura cut the ball back and it was not cleared properly, but Pereyra could only fire his shot over the bar from 15 yards.
Zemura was involved again when he sent a pass across the face of the Milan goal following a free-kick, but no-one was able to get a telling touch.
The Rossoneri, missing Theo Hernandez through an ankle problem, finally showed some signs of life when Rade Krunic headed wide from a corner and then Davide Calabria had his shot beaten away by Udinese keeper Marco Silvestri.
American midfielder Yunus Musah again tested Silvestri with a fierce drive.
Alessandro Florenzi was unfortunate not to be rewarded for a fine piece of individual skill when he took a pass from Rafael Leao and spun around on to goal, but could not find a finish.
AC Milan made a couple of changes for the second half as Yacine Adli replaced Krunic and Swiss forward Noah Okafor came on for Luka Jovic, who looked to have picked up an injury.
Udinese wasted another chance to break the deadlock when a corner was flicked on to the back post, where defender Christian Kabasele lashed it over from close range.
The hosts then broke quickly as Okafor was sent clear, but his chipped effort over the on-rushing Silvestri dropped wide.
On the hour, Udinese were awarded a penalty when Festy Ebosele went down as he got in between Tijjani Reijnders and Yacine Adli, which was backed up by a VAR review.
Pereyra kept his cool to send Milan keeper Mike Maignan the wrong way as he rolled the ball into the bottom right corner.
Pioli made another change to try to spark his Milan side, with fit-again midfielder Ruben Loftus-Cheek coming on for a first appearance since the end of September.
It was Udinese, though, who then almost grabbed a second when Isaac Success’ downward header from a corner was palmed away by Maignan.
Milan pushed for an equaliser, with Rafael Leao threatening down the left before Florenzi lashed a shot high over the crossbar when a corner was cleared out to the edge of the box.
In the 89th minute, a deep cross from the left by Leao found Olivier Giroud, who diverted the ball towards the top corner off his shoulder, but Silvestri made a superb save at full stretch.
Silvestri tipped away a rising drive from Florenzi and Leao flashed a 20-yard drive just wide as Milan pressed in during seven minutes of stoppage time.
There was, though, to be no late reprieve as boos rang out from the disgruntled home fans at the final whistle while Udinese joyously celebrated a memorable first win under new manager Gabriele Cioffi.
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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