AC Milan and Napoli meet again in the Supercoppa Italiana on Thursday in Riyadh, with a place in the final against either Inter or Bologna at stake. Milan enter the semi-final in strong domestic form, yet Massimiliano Allegri is preparing for a demanding test against opponents separated by just two points in Serie A.
After 15 Serie A rounds, Allegri’s side sit second, one point behind leaders Inter, and have not lost since an opening-day defeat to Cremonese. Napoli trail Milan by a single point, keeping the title race tight ahead of their Supercoppa Italiana clash, which comes four months after their league meeting.
The September league game saw Milan beat Napoli 2-1, despite playing with 10 players for much of the second half after Pervis Estupinan
was dismissed early in that period. Milan had built a 2-0 advantage through goals from Alexis Saelemaekers and Christian Pulisic, and Allegri’s team then resisted Napoli’s late pressure.
That result continued a largely balanced run between the clubs. Across the last 20 head-to-head matches in all competitions, Milan and Napoli have each collected seven wins, with six draws. However, Milan have avoided defeat in six of the last eight encounters, winning four and drawing two, although both Napoli victories came in Serie A last season.
Milan now have the chance to record consecutive wins over Napoli for the first time since April 2023, when Allegri’s side won 4-0 in Serie A and 1-0 in the Champions League. Yet preparation for the Supercoppa Italiana Milan vs Napoli tie is complicated by injury concerns for Rafael Leao, who missed Sunday’s 2-2 draw with Sassuolo.
Leao sat out that match due to a minor muscle issue and has not yet returned to full training. The Portugal international has six goals and one assist in all competitions, giving seven goal contributions. Only Pulisic has surpassed that for Milan this season, with nine goals and two assists across all tournaments.
Allegri is ready to give Leao every opportunity to feature against Napoli. "We'll see if he becomes available," Allegri said. "He hasn't trained with the team for several days, so today we'll evaluate his condition. " The coach knows losing such an important forward would affect Milan’s attacking options in Riyadh.
Allegri expects a very different contest from September’s league meeting, stressing the single-elimination nature of the Supercoppa Italiana Milan vs Napoli match. "Tomorrow will be a different game, it's a one-off match where the goal is to get to the final," Allegri said. "Napoli are a very strong team. It will be a complicated and difficult match. "
The coach highlighted Napoli’s threat inside the penalty area and recent intensity against Serie A rivals. "Napoli, regardless of the tactical aspects, are a strong team, who score a lot of goals from inside the box. Tomorrow will be a new, beautiful match, with quality players. They were very aggressive in the games against Juventus and Roma. We have to be good technically; we have to play well. "
Allegri also addressed questions over potential January moves, including reports linking Milan with West Ham striker Niclas Fullkrug. The coach underlined that returning injured players remains the main objective, saying: "Milan's most important market is to recover the players we have available to us, then we will see what we can do on the transfer market, together with the club. "
Recent Serie A performance underlines why Allegri wants stability rather than major changes before the Supercoppa Italiana Milan vs Napoli showdown. Milan are unbeaten in 14 league matches since losing to Cremonese, while Napoli remain close behind in the standings, leaving Thursday’s meeting as another key test of both teams’ ambitions in Italy and beyond.
