AC Milan begin the defence of their Supercoppa Italiana crown tonight, taking on Antonio Conte’s Napoli in the semi-final in Saudi Arabia.
While the Supercoppa might not be the number one target for any club going into a season, it certainly brought joy to Milan during a 2024-25 campaign that was riddled with disappointments otherwise.
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The winner would advance to the final to play the winner of Bologna versus Inter, and the Rossoneri have the chance to potentially equal Juventus’ record of nine Super Cup titles. Against a Conte side though, it will not be easy.
Milan are not in the best of shape physically, given that Matteo Gabbia has a knee issue, Santiago Gimenez is heading for ankle surgery, while Youssouf Fofana is fit enough only to make the bench and there is mystery surrounding Rafael Leao’s involvement.
Napoli vs. AC Milan: Five key battles
The two sides are expected to line up in similar systems: a 3-4-2-1 for Napoli and a 3-5-2 for Milan. This, the midfield and the flanks will become crucial. In the middle of the park, there will be a battle between Stanislav Lobotka and Luka Modric, who will be in opposing engine rooms even if not directly facing each other.
Both will face the task of trying to set the pace of play with their building out from the back, but at the same time must shield the three-man defence behind them. Modric’s important to Milan cannot be overstated, though in recent games he has looked a tad rusty. Whoever dictates from deep could have the keys to the game.
This is a big night for Koni De Winter and Rasmus Hojlund. There is something that unites them in the fact that Milan took a strong look at signing both players in the summer window, but the difference is that the former actually signed from Genoa while the latter headed for the Italian champions.
De Winter has disappointed so far when he has stepped in, but with Gabbia absent he simply has to step up this time. Hojlund meanwhile has netted six times this season and he faces a battle to prove to Conte that Romelu Lukaku shouldn’t go straight back into the team when he is fully back from injury.
On the Rossoneri’s left side, an intriguing duel beckons between Davide Bartesaghi and Matteo Politano. It is believed that Conte has opted for the latter to try and pin Bartesaghi back and generate some more attacking threat, with another full-back in Giovanni Di Lorenzo asked to cover as a right-sided centre-back.
It has been a dream few weeks for Bartesaghi, with the 19-year-old having nailed down a starting spot thanks to a series of great performances, and then netting his first two goals for the club in the 2-2 draw with Sassuolo. That alone shows he carries a threat going forward, so it could be a real back-and-forth contest down that side.
Moving back to the midfield, there will be and English versus Scottish rivalry in the mezzala positions, with Ruben Loftus-Cheek coming up against Scott McTominay. The Napoli man needs little introduction as he was rightly the league MVP in a season that led to league title glory, and he remains their main threat with his crashing runs into the box, even when in a double pivot.
Loftus-Cheek meanwhile faces an interesting crossroads. He has found himself as a starter recently both up front and in midfield with Fofana out, yet he hasn’t really nailed down a solid position. With rumours swirling of a potential January sale, keeping McTominay quiet in the physical battle and providing service into the front two could show Allegri that he should be a central part of the plans.
Finally, we end with a duel between two players quite literally at opposite ends: Mike Maignan and Vanja Milinkovic-Savic. There is a sliding doors moment here too, given that the Serbian was earmarked as a replacement for Maignan if he had beens old to Chelsea, but ended up at Napoli where he has alternated with Alex Meret, who is currently out injured.
With the Frenchman, a lot of the headlines at the moment concern a possible renewal, especially after some decisive performances in big games. Given that there is no extra-time, it cannot be ruled out that the two men with the gloves end up having the final say in this knockout tie, with a penalty shootout on the cards in the event that the game is level after 90 minutes.
