Milan dropped potentially crucial points in their bid to win Serie A after they were frustrated by Bologna in a 0-0 draw at San Siro.
The Rossoneri went into the international break holding a three-point lead on the back of three straight 1-0 wins, but they could not keep up that winning run on Monday.
Indeed, Bologna – whose coach Sinisa Mihajlovic was not present on the touchline as he is in hospital for leukemia treatment – restricted Stefano Pioli's team to little in the way of clear chances in their boss' 100th league match in charge, to the chagrin of an expectant Milan faithful.
With Napoli and Inter having both won on Sunday, Milan's advantage has now been cut to just one point with seven games remaining.
Rafael Leao had the first opportunity 16 minutes in, though the Portugal forward could not keep his shot down.
Michel Aebischer drilled straight at Mike Maignan following Marko Arnautovic's clever dummy, before Milan's goalkeeper tipped Musa Barrow's strike over after Gary Medel had made a fine block at the other end.
Bologna continued to frustrate their hosts after the restart, with Leao particularly wasteful, first skewing a cross out of play before failing to get a shot off when he had space.
Leao provided a sublime pass for Davide Calabria in the 61st minute, but Medel just managed to divert the full-back's shot wide – a touch the referee failed to notice.
Ante Rebic blazed over as Milan kept up the pressure, with Leao then curling wide from just inside the area.
Zlatan Ibrahimovic was given 20 minutes to try and make a difference, but the veteran headed over from the one chance that came his way as Milan were thwarted.
What does it mean? No milestone celebration for Pioli as pressure mounts
Pioli did not look longed for the Milan job early in his tenure, but the work he has done to turn the Rossoneri into genuine title contenders has been quite superb. Yet, his milestone 100th Serie A game in charge did not end in a victory, but instead a draw that could prove decisive.
Inter battled their way to a 1-0 win over Juventus on Sunday and are just four points back with a game in hand, while Napoli, who like Milan have played 31 times, are only a point behind the leaders. Bologna, meanwhile, did their coach Mihajlovic proud.
Medel leads brilliant Bologna rear-guard
Medel spent time at San Siro with Inter and the experienced, dogged defender was excellent at the heart of Bologna's defence, doing his old side a huge favour in the process.
He made a joint team-high two blocks, including a fantastic one from Diaz in the first half, gained possession seven times and kept things simple on the ball, completing 33 of 36 passes before he had to go off with a head injury following a collision with Ibrahimovic.
Leao found lacking as Milan pay for their profligacy
It has been a fine season for Leao overall, with the 22-year-old scoring eight league goals so far.
His finishing was found totally lacking this time out, however, with only one of his eight attempts hitting the target, while four were blocked. His wastefulness summed Milan up, as the hosts tallied up 33 attempts to no avail.
What's next?
Milan travel to Torino on Sunday, while Bologna host Sampdoria.
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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