A weakened Milan side were held to a 1-1 draw in Serie A by Bologna at the Stadio Renato Dall'Ara.
With their focus clearly on the second leg of the Champions League quarter-final tie with Napoli, Stefano Pioli's side made 10 changes and fell behind to a Nicola Sansone strike inside the opening minute.
The early goal sparked some life into Milan's understudies, with Tomasso Pobega's fierce strike levelling the scores before the break.
Neither side could find a winning goal in the second half, with honours even and a result Bologna will be happier with.
Milan heavily rotated from the opening leg win against Napoli, only Mike Maignan retaining his spot between the posts, and he was picking the ball out the back of the net after just 33 seconds when Sansone met Stefan Posch's low cross and smashed home.
The visitors responded strongly, dominating possession, with Ante Rebic heading straight at Lukasz Skorupski before the Bologna shot stopper was forced into a diving save from Alessandro Florenzi's curling free-kick.
Milan's equaliser came five minutes before the break, Bologna unable to clear their lines properly and Pobega unleashing a fierce shot that cannoned off the inside of the left-hand post and into the back of the net.
A much quieter second half saw limited clear-cut opportunities for both sides, with Milan's attempts to pepper Skorupski's goal seeing a number of efforts fail to provide any sort of threat to the Polish keeper.
Rebic came closest to an equaliser, though not through skill as the chance instead saw an attempted clearance strike his head but fly wide of the mark, much to the relief of the home side.
Sinner reaches 250 career wins after seeing off Daniel in Shanghai opener
Jannik Sinner notched up his 250th career win after defeating Taro Daniel in his Shanghai Masters opener.
The world number one wrapped up a commanding 6-1 6-4 victory over his Japanese opponent in just over an hour-and-a-quarter on Saturday.
Sinner, who is fresh from reaching the Beijing final last time out, is targeting his seventh silverware of the season, in which he has already triumphed at the Australian Open and US Open.
"I felt quite comfortable today," said the Italian, who set up a clash with 31st seed Tomas Etcheverry. "I also feel in good shape physically, which is very important for me.
"Of course, I will try to improve for tomorrow's performance, but today I was serving really, really well - especially in important moments - and was moving well."
Data Debrief: 250 up for Sinner
Sinner became the first player born in the 2000s to reach 250 career wins, while taking his tally for a remarkable campaign to 60.
The Italian, who won 64 matches last term, is the sixth player aged 23 or under to record 60 or more ATP wins in successive seasons, after Lleyton Hewitt, Andy Roddick, Roger Federer, Rafael Nadal and Novak Djokovic.
Sinner also maintained his perfect record in opening-round matches this year (14-0), and is now 51-0 against players ranked outside the ATP top 20.
Eidevall slams 'amateurish' WSL after Arsenal fixture congestion
Arsenal head coach Jonas Eidevall slammed the "amateurish behaviour" of the Women's Super League, who he feels are damaging English teams' chances of success in European competition.
The Gunners are one of three English teams competing in the Women's Champions League group stages this season, along with Manchester City and Chelsea.
All three are due to commence their campaigns in midweek, but while Arsenal and City are in WSL action on Sunday, Chelsea's scheduled clash with Manchester United was postponed due to player welfare concerns.
Eidevall's side, who face Bayern Munich on Wednesday, then take on the Blues three days later, and the head coach feels his side are at a "sporting disadvantage" with their fixture congestion.
"It's not a good situation," he told reporters during his pre-match press conference ahead of Sunday's clash with Everton. "There are 16 teams involved in the Champions League, how many teams are playing on Sunday, October 6?
"We are, that is one. If it was only us, it would be an Arsenal problem - but it's also Man City. The only two teams that are playing are English teams. The only other team scheduled to play was Chelsea.
"[It's the] first time that three [English] teams reach the group stage. [It] should be celebrated, but it's now a problem. It's very important for the whole league that we are successful in Europe.
"Now, obviously, it's worse for us because of the amateurish behaviour of no plan and taking away the game like Chelsea.
"It puts us into play on Sunday, then Wednesday away at Bayern Munich, who don't play Sunday, then we return to play Chelsea on Saturday (October 12).
"[That is] less preparation than our opponents. We have been handed a sporting disadvantage in two huge games for us."
Nevertheless, Eidevall insists his players will tackle the busy period head on, rather than feel sorry for themselves.
"We won't lie down and give up because the situation is tough," he said. "We will dig deeper than we ever have before, but what needs to change is the approach to Champions League football and respect to the supporters.
"It's not good enough to blame UEFA, the only one who hasn't acted on the information is the WSL."
Premier League rejects Man City request to delay 2025-26 season start
The Premier League has rejected a request from Manchester City to delay the start to their 2025-26 campaign to allow for more recovery time after the Club World Cup.
As 2022-23 Champions League winners, City are one of two English clubs – alongside Chelsea – to have secured a spot at FIFA's first 32-team Club World Cup, which will be held in the United States next year.
The tournament's expanded format has proven extremely controversial, provoking widespread criticism for denying players rest time during the off-season.
Players' union Fifpro has started legal proceedings against FIFA over the scheduling of the tournament, claiming the fixture schedule has become "unworkable".
The Club World Cup is set to run from June 15 to July 13, with players involved unlikely to receive substantial rest time before the domestic season begins in early August.
Speaking ahead of Saturday's Premier League clash with Fulham, boss Pep Guardiola revealed City had already seen a request to delay their opening game knocked back.
"The Premier League has not allowed us to postpone the first two games for our recovery," Guardiola said. "Thank you so much.
"I think the club asked the league to postpone one or two or three weeks so we can have a holiday after the [Club] World Cup but it is absolutely not allowed.
"Would the Premier League say yes to us? No. Absolutely not. They won't postpone these games so there will be a moment of, 'what do we do?
"I don't have an answer right now but we are going to take a decision with common sense."
SportsMax is the Caribbean sports channel of choice, committed to providing sporting content of the highest quality to the Caribbean, delivered by a team of highly innovative, passionate and qualified professionals.
(876) 619-7629
digitalmedia@sportsmax.tv
