Coach Gennaro Gattuso is on the hot seat after three draws in a row, and the former midfielder needs to inspire his troops for this tough away trip to Sassuolo.
As for I Neroverdi, their early season form has risen beyond expectation. Currently sitting pretty in third place, Roberto De Zerbi's side are knocking down all comers.
With their only loss coming against champions Juventus, 13 points for a possible eighteen is very impressive. Potentially challenging for the Europa League spots this campaign, strong home form will be crucial.
Sassuolo 4-3 AC Milan (Serie A, January 2014)
The first ever clash between these two teams resulted in an absolute humdinger, with Domenico Berardi playing a starring role. Grabbing all four of Sassuolo's goals, the diminutive Italian stunned AC Milan in a match that ebbed and flowed like crazy.
Up 2-0 thanks to Robinho and Mario Balotelli, I Rossoneri were hit with a furious comeback. A remarkable 36 minute hat-trick from the aforementioned Berardi saw his side finish the half ahead.
It didn't take Berardi long to add to his tally after the break either, sweeping home Jasmin Kurtic's cross a mere 120 seconds in.
A late finish from Riccardo Montolivo saved the Milan powerhouse from complete embarrassment, but his side couldn't find another before the final whistle.
Rogerio vs Suso
Sassuolo's Brazilian warrior is in the second year of his loan spell from Juve, and has shown legitimate quality. Appearing for his national side at Under-20 level, Rogerio's ability should afford him a chance at making the Selecao soon.
Suso, perhaps the only bright spark at Empoli, could've found himself on the score sheet multiple times if not for goalkeeper Pietro Terracciano. Up against an in form full back this time out, the Spaniard's agility and speed could unlock the door for AC.
While left back Fedrico Peluso is out, Alfred Duncan and Kevin-Prince Boateng should recover from niggling injury problems after missing the midweek victory against SPAL.
Sassuolo coach Roberto De Zerbi will also have Pal Lirola, Manuel Locatelli, and star man Berardi all raring to go at Mapei Stadium after granting rests on Wednesday.
A Turtle > Borini— 🔴⚫️ (@Milan4eva1026) September 28, 2018
The big news coming out of Milan's camp is that Gonzalo Higuain is unlikely to recover from a knee flexor problem in time for this weekend.
Bad news for a side that desperately need goals, Gattuso will now need to choose between a recovering Patrick Cutrone or the out of form Fabio Borini to lead I Rossoneri's line.
Mattia Caldara is to miss out yet again with a muscular injury, meaning that the shaky partnership of Alessio Romagnoli and Mateo Musacchio will patrol central defence.
Potential Sassuolo Lineup (4-3-2-1): Consigli; Lirola, Marlon, Ferrari, Rogerio; Locatelli, Sensi, Duncan; Berardi, Di Francesco; Boateng.
Potential AC Milan Lineup (4-3-3): Donnarumma; Calabria, Musacchio, Romagnoli, Laxalt; Kessie, Biglia, Bonaventura; Suso, Borini, Calhanoglu.
Without Higuain up top. it's going to very hard for Milan to score. Sassuolo have proven throughout the early part of this season that they are no joke, and trying to stop Borini shouldn't fill them with fear either.
Defensively I Rossoneri are shoddy, as continued individual mistakes keep costing them points. They lack any sort of cohesion, so coming up against the current top goalscorers in Italy isn't good news.
To summarise, Milan are bad. This could well be Gattuso's last game in charge.
Prediction: Sassuolo 2-0 Milan