Supercoppa Italiana – Semifinal: Napoli v Milan

I’ve spent a lot of blog real estate the last few weeks on talking about the concerning trend of Milan dropping points and seemingly unable to beat lower table teams on a consistent basis. All of those critiques still stand AND they don’t really apply to today’s game. Why? Well, it’s because the potential opponents in this 4-team tournament all match up well against Massimilano Allegri’s preferred tactical approach.

Today’s game and indeed in the Supercoppa final should they make it, will be against teams that don’t sit back and have a little offensive punch. This allows Allegri, both tactically and psychologically, to commit to sitting back in a very defensive posture and playing rather boring conservative football. This helps keep you in the game and you can sting teams against the run of play then go back to the defensive posture. This doesn’t work vs smaller teams because they want to sit back too and are more willing and content to take home a point as every one is valuable to avoiding relegation. So Milan has struggled against these teams because Allegri can’t bring himself to commit to aggressive offensive football. One last thing on this: this Allegri approach is good for few loses and generating draws that can help a league campaign (although not win it per se), it’s less helpful in tournaments where you actually have to win.

As for this game, there’s been some uncertainty about who’s going to start and in the case of Rafael Leão and Mattia Gabbia, who’s going to be available. Santiago Giménez had surgery and is out 2 months, combined with Leão possibly unavailable or at least unavailable to start, the frontline is almost certainly going to be Pulisic and Nkunku. The other unknowns are Fofana and if Allegri starts Modrić, who has logged the most minutes of any player on the squad (not ideal for a 40yr old). I really hope to see Jashasi start or at least play since I thought we’d get that last game and he never even sniffed the grass.

As for Napoli, they come in limping some with Anguissa and De Bruyne out until early 2026. But they are deep enough at least to start to have a strong lineup and threaten Milan if they aren’t careful. The last time these two teams played, Napoli didn’t do anything until Estupiñan was sent off and only then scored on a weak penalty. With Conte’s Napoli needing to attack Allegri’s Milan, which is what happened in the first meeting, that takes him out of his preferred defensive posture and they aren’t as good or dominating (remind you of anyone?…). Maybe we see both coaches sit back, daring the other to come out of their shell? How exiting for us fans…