A terrible week off the field for AC Milan was compounded by a humiliating defeat on it after the Rossoneri surrendered a lead to lose 2-1 to Sassuolo.
After Milan officially pulled out of the Super League earlier on Wednesday, full attention turned to a potentially tricky fixture.
Despite the absence of Zlatan Ibrahimovic, who failed a fitness test and missed out on the match day squad, Milan made a bright start as Hakan Calhanoglu broke the deadlock with a beautiful curling effort in the 30th minute.
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Milan required Diogo Dalot to make a last-ditch block to deny Domenico Berardi as Sassuolo responded positively and the visitors fired another warning when Hakim Traore flashed a shot just over from a tight angle after the restart.
With Sassuolo throwing bodies forward in attack, they were finally rewarded when substitute Giacomo Raspadori poked home from close range with under 15 minutes remaining after Jeremy Toljan's shot was deflected into his path.
But things went from bad to worse for Milan as Raspadori scored a quick-fire second, finding the net seven minutes later with a smart finish to sensationally win the game for the visitors.
The result all but ends Milan's title hopes as they are now nine points behind leaders Inter having played a game more and Antonio Conte's side will move 12 points clear with a win at Spezia later. And on Thursday evening, fifth-placed Napoli will be targeting a victory over Lazio that could move them to within three of Milan.
TALKING POINT - Sassuolo inflict damaging defeat on one of the 'Dirty Dozen'
With the Super League proposal dominating the build-up to this contest in Italy, Sassuolo wanted to remind the world just how competitive Serie A is. Mission accomplished. They may have a wage bill the fraction of Milan's but for large parts of the game they looked the superior side. And the final result reflects that.
This was just another reminder of why football fans across the world were so strong in their condemnation of a breakaway league, as a so-called lesser club inflicted a damaging defeat on one of the so-called elites.
Not only does it effectively end their scudetto dreams but it could also spell trouble in their aspirations of ending a seven-year wait to play in the Champions League.
MAN OF THE MATCH - Giacomo Raspadori (Sassuolo)
He may have only played half an hour but the promising Italy U21 star showed a clinical edge, scoring twice to win the game for his side.
Milan: Donnarumma 5, Calabria 5, Kjaer 5, Tomori 5, Dalot 6, Meite 5, Kessie 6, Saelemaekers 7, Calhanoglu 8, Rebic 6, Leao 4.. subs: Kalulu N/A, Castillejo N/A, Diaz N/A, Krunic 5, Mandzukic 5.
Sassuolo: Consigli 6, Muldur 7, Marlon 7, Ferrari 7, Kyriakopoulos 7, Obiang 8, Locatelli 8, Berardi 7, Djuricic 6, Boga 7, Defrel 6.. subs: Toljan 7, Lopez 5, Traore 6, Haraslin N/A, Raspadori 8*.
30' - GOAL! Milan 1-0 Sassuolo (Hakan Calhanoglu): Stunning goal! Saelemaekers carves in from the left flank and rolls the ball to Calhanoglu on the edge of the penalty area. The overlapping run from Dalot creates the space for him to shoot, and he makes no mistake, curling an unstoppable effort that nestles in the top far corner.
76' - GOAL! Milan 1-1 Sassuolo (Giacomo Raspadori): The visitors are level! Toljan is left unmarked on the right side of the penalty area and he's picked out by Raspadori's pass. His shot is deflected but Raspadori reacts quickest to poke it past Donnarumma!
83' - GOAL! Milan 1-2 Sassuolo (Giacomo Raspadori): Oh wow! Sassuolo are ahead! The highly rated Raspadori grabs a brace and potentially the winner! Berardi carves inside and picks out Raspadori in the middle. He takes a nice touch to beat Tomori and applies the finish!
Giacomo Raspadori is the first player to score a brace as substitute vs AC Milan in Serie A in the three-points-for-a win era (since 1994/95).
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