A goal and two assists from Italy international Domenico Berardi piled on the misery for Milan as Sassuolo thrashed the Rossoneri 5-2 at San Siro.
Sassuolo took an early two-goal lead thanks to goals from Gregoire Defrel and Davide Frattesi prior to Olivier Giroud pulling one back for the hosts.
Berardi made it 3-1 after just 30 minutes before Armand Lauriente's penalty and Matheus Henrique's effort in the second half handed Milan their second chastening loss in a week after their 4-0 humbling at Lazio on Tuesday.
Divock Origi scored a consolation for Stefano Pioli's side, who are now six games without a win heading into next weekend's Milan derby, including four in Serie A as their title defence continues to falter.
A VAR review denied Giroud an eighth-minute opener and, to make matters significantly worse, Milan found themselves two down inside 22 minutes.
Berardi squared for Defrel to tap in the opener before the same man fed Frattesi, who fired past Ciprian Tatarusanu at his near post after great work in the area.
Milan provided a swift response when Giroud expertly headed Davide Calabria's cross into the far corner in the 25th minute.
But the two-goal lead was restored on the half-hour mark when Berardi flicked a near-post header past Tatarusanu from a corner.
Milan's hopes of a second-half comeback were doused almost immediately as Lauriente was brought down in the penalty area by Calabria after 33 seconds of the restart, allowing the Frenchman to make it 4-1 from the spot, meaning Milan had conceded at least four goals in back-to-back Serie A games for the first time in their history.
Ante Rebic had a goal ruled out for offside before Henrique fired in a fifth with just over 10 minutes remaining, with Origi's curling strike into the top corner doing little to lift the gloom among the home fans.
Dundee boss Tony Docherty excited by Scott Tiffoney signing
Dundee boss Tony Docherty is “thrilled” by the recruitment of Scott Tiffoney as he gears up for the cinch Premiership next season.
The winger has agreed to join the newly-promoted Tayside club when his contract with Partick Thistle ends at the weekend.
Tiffoney was in the Jags side which lost to Ross County in the Premiership play-off final.
Docherty, who took over as Dundee boss last week, told the club’s official website: “I am thrilled that Scott will be joining the club. He is a player that I have monitored and admired for a long time and is a player that will get the fans off their seats.
“When he has the ball, he can make things happen, he can create chances for others, and he can create opportunities for himself.
“He has a tremendous work ethic and wants to improve as a player.
“He is committed to the club and will be moving up here and I’m really excited about having him at the club.”
Tiffoney began his career with Greenock Morton before moving to Livingston in 2018 and then to Partick Thistle.
He has also had loan spells at Clyde, Morton, Ayr and Partick Thistle.
Football rumours: Tottenham eye move for Harry Maguire in bid to keep Harry Kane
What the papers say
Manchester United defender Harry Maguire, 30, has emerged as a target for Tottenham, according to The Daily Telegraph. The London club are hoping the signing could help persuade his England colleague Harry Kane to stay at the club as big-name clubs line up for his signature.
Maguire is one of eight players United are looking to move on this summer, reports the Daily Mirror. Striker Anthony Martial, 27, Scott McTominay, 26, fellow midfielder Fred, 30, and goalkeeper Dean Henderson, 26, are also on the list, along with defenders Eric Bailly, 29, Alex Telles, 30, and Brandon Williams, 22.
Brighton want more than £70 million for Manchester United target Moises Caicedo, says The Daily Telegraph. Chelsea and Arsenal are also chasing the 21-year-old Ecuador midfielder.
Chelsea midfielder N’Golo Kante, 32, is wanted by two clubs in Saudi Arabia, according to The Guardian. Al-Ittihad and Al-Nassr are keen on the France star with annual salary offers which could reach £86.2 million.
Social media round-upPlayers to watch
Levi Colwill: The Daily Mail reports Brighton are considering an increased bid of around £40 million for the Chelsea defender, who spent last season on loan at The Seagulls.
Gabri Veiga: Chelsea have joined Liverpool and Barcelona in tracking the Celta Vigo midfielder, 21, who has a £34.4 million release clause, says The Guardian.
On this day in 2016 – Chelsea and Jose Mourinho settle Eva Carneiro claim
Chelsea and Jose Mourinho reached a settlement with former team doctor Eva Carneiro over her claims that she was constructively dismissed by the club, and victimised by its former manager, on this day in 2016.
Carneiro had brought the claim at an employment tribunal, accusing Mourinho of victimisation and discrimination. She was due to begin giving evidence but after last-minute talks between the parties, a settlement was agreed.
Mourinho made a surprise appearance at the hearing at the London South Employment Tribunal centre in Croydon.
Addressing the tribunal, Daniel Stilitz QC, for Chelsea and Mourinho, said: “We are pleased to be able to tell the tribunal that the parties agreed a settlement on confidential terms.”
The case was expected to last seven to 10 days and could have led to potentially embarrassing witness statements and documents – including texts and emails – being made public.
It was revealed that Carneiro had refused £1.2 million to settle her claims with Mourinho and Chelsea. Details of the final deal between the parties were not released.
Carneiro had alleged she was sexually discriminated against after she went on to the pitch to treat Eden Hazard during the opening day of the Premier League season on August 8, 2015.
She claimed that, as she ran on to the pitch during the game with Swansea, Mourinho shouted “filha da puta” at her.
In a statement to the tribunal, Mourinho conceded that he used the term “filho da puta”, meaning “son of a whore”, but insisted he had been using it throughout the match.
Carneiro was removed from first-team duties at Chelsea shortly after the Swansea game and then parted company with the club the following month.
Chelsea said in a statement: “The club regrets the circumstances which led to Dr Carneiro leaving the club and apologises unreservedly to her and her family for the distress caused.
“We wish to place on record that in running onto the pitch Dr Carneiro was following both the rules of the game and fulfilling her responsibility to the players as a doctor, putting their safety first.
“Dr Carneiro has always put the interests of the club’s players first. Dr Carneiro is a highly competent and professional sports doctor. She was a valued member of the club’s medical team and we wish her every success in her future career.”
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