Sassuolo sit 10th on seven points from five matches, two wins, one draw and two defeats, while Milan arrive fifth with 11 points, still unbeaten and having conceded just four goals. Sassuolo need this to climb the table and both managers will be navigating it as strangers, meeting in competitive football for the first time.
Sassuolo's form has been a study in feast and famine. Their best result this season came on 13 September when they beat Juventus 3-2, a result that showed they can compete with the top sides even if they haven't done it consistently since, with their other four results split between defeats and draws. Milan, by contrast, have conceded just four goals across their last five Serie A outings, capped by a 3-0 dismantling of Lecce just before the international break.
Alberto Aquilani, who replaced Fabio Grosso in June, is dealing with a lengthy injury list that's making selection complicated. Arijanet Muric is a doubt after international duty and Sebastian Walukiewicz is a further doubt with a muscle issue, while Jay Idzes, Fali Cande, Edoardo Pieragnolo, Ismael Kone, Daniel Boloca and Cristian Volpato are all ruled out through injury. The sheer number of absentees forces Sassuolo into defensive reshuffles and leaves them thin in midfield. Amorim, who replaced Massimiliano Allegri in mid June, has fewer problems: Alexis Saelemaekers is out until around 2027 following ankle surgery and Pervis Estupinán is a doubt with a knee sprain picked up on international duty, though those absences merely thin their wide options and the squad depth means Amorim has cover.
Sassuolo tend to line up in a 4-3-3 or a flexible variation on that shape and against stronger sides they push their intensity up a level, as the Juventus win showed. Domenico Berardi is historically a pain for Milan, Armand Laurienté operates alongside him in wide areas and Sebastiano Esposito leads the line as their central striker. With no clean sheet in their last six matches and central midfielders and defenders missing, there's a structural problem in protecting the back line when possession turns over, particularly with Boloca, Kone and Idzes all absent.
Milan operate on possession dominance with a high press, shifting between a 3-4-2-1 and back four setups depending on the opponent. Their defensive numbers reflect disciplined positioning and quick recovery rather than luck, with four goals conceded in five matches making that point more plainly than any tactical description could. Pulisic operates in the spaces between lines behind the striker, Goncalo Ramos leads the line and the midfield pairing of Adrien Rabiot and Luka Modric gives Amorim experience and composure in the middle of the pitch. The doubt over Estupinán may prompt some adjustment on the left side but the overall structure will stay the same.
Berardi against Milan's right side is Sassuolo's clearest route into the game and Esposito's movement will test whether the visitors' back line holds up under pressure. With Boloca, Kone and Idzes all missing though, the service those two need from midfield is the real problem for Aquilani to solve.
Sassuolo won the most recent meeting 2-0 at home in May 2026 and two of the last three Serie A encounters ended level. Across 26 meetings overall, Milan have the edge with 13 wins to Sassuolo's eight, with five draws but with Sassuolo taking the most recent meeting and half the recent run ending all square, this isn't a ground Milan have dominated.
With Sassuolo missing defensive height and organisation, Milan's delivery from dead balls, Modric in particular, is a specific danger that hits them at exactly the wrong time given the absences at the back. Sassuolo's tendency to concede on the transition after losing possession may also push them toward cautious build up play, which plays into Milan's hands rather than out of them.
Milan to win 2-1. Berardi and Esposito will cause problems (the Juventus result showed what this attack can do) but they need service that a depleted midfield may not consistently provide. Sassuolo's injury list, particularly in midfield and defence, is the deciding factor and Milan are too well-organised to be beaten by a side this depleted.
Ryan Baldi
Football Writer
Ryan Baldi is a professional football writer with years of experience and has been featured by respected outlets such as the BBC, The Guardian, Sky Sports, DAZN, FourFourTwo, ESPN, Yahoo Sport and Football365. He has also written several books including Arsène Who?.
