Milan and Napoli meet face to face, far away from San Siro and the Stadio Diego Armando Maradona, with a crucial slice of their season on the line. In Riyadh, at Al-Awwal Park (King Saud University Stadium), the Italian Super Cup semi-final takes centre stage: on one side the reigning Serie A champions, on the other the holders of the trophy, who one year ago in Saudi Arabia kicked off a new era by lifting the 50th title in the club’s history.
It is the first ever meeting between Milan and Napoli in the Supercoppa, and it comes at a time when both teams are trying to rediscover consistency after a few bumps in the league and in Europe. For Massimiliano Allegri, this is a chance to turn the Supercoppa into the first real trophy of his second spell with the Rossoneri; for Antonio Conte, it is an opportunity to round off an intense 2025 by bringing another piece of silverware back to Naples after putting the team firmly back in the Scudetto race.
Conte walking the line between fatigue and ambition
After a run of five straight wins, Napoli have hit a bump in the road with two heavy defeats, against Benfica in the Champions League and Udinese in Serie A, in both cases struggling to make any real impact in the final third.
The most worrying figure is the gap between home and away form. At the Diego Armando Maradona stadium, Antonio Conte’s side have just completed a full calendar year without losing, while away from Naples they have already suffered seven defeats this season, including six of the eight Serie A losses recorded under the coach from Lecce.
Napoli arrive in Riyadh with a clear target: to win the third Supercoppa in their history, after the triumphs in 1990 and 2014. Conte knows that lifting a trophy in mid-season can become emotional fuel for the run-in. Right now the Partenopei are chasing Milan and Inter by only a few points, but the balance at the top of the table means every detail could prove decisive.
The news from the treatment room is not entirely negative. Romelu Lukaku has finally returned to full training after four months out and could start on the bench, ready to come on if the game demands it. On the other hand, Alex Meret is ruled out, as is the midfield trio of Kevin De Bruyne, Frank Anguissa and Billy Gilmour – a cluster of absences that deprives Conte of a great deal of quality and physical presence in the middle of the park. In the meantime, Rasmus Højlund has carried the attacking burden on his shoulders, racking up eight goal involvements between goals and assists in all competitions.
In Saudi Arabia the Dane is expected to lead the line in Conte’s 3-5-2/3-4-2-1, with the front line completed by the creativity of Noa Lang and the one-on-one ability of David Neres.
Milan’s current moment: defending champions looking for a new spark
For Milan, the Supercoppa is not just a trophy to defend, but also a chance to reset emotionally. The Rossoneri arrive in Riyadh as title holders, having lifted the cup last January by coming from behind to beat Juventus in the semi-final and then Inter in the final. That night, celebrated as the 50th trophy in the club’s history and the crowning moment of the 125th anniversary year, now feels a long way away: both staff and squad have been almost completely rebuilt since those scenes of celebration.
The arrival of Massimiliano Allegri has brought back solidity and pragmatism, but the path has been anything but straightforward. Milan crashed out of the Coppa Italia earlier than expected, struggled in a few away fixtures and, on the eve of this trip to Saudi Arabia, dropped two huge points against Sassuolo: from 2–1 up after a comeback to a 2–2 draw, despite a dream night for youngster Davide Bartesaghi, who scored a brace from left wing-back in the 3-5-2.
After six consecutive clean sheets at the start of the season, the Rossoneri backline has gradually lost some of its solidity, keeping a shut-out only four times in the following twelve matches and conceding too much to so-called smaller sides.
On the positive side, Milan are still fully in the Scudetto race and have yet to lose away from home this season – a statistic that helps to soften the impact of those recent draws.
The club’s stated objective is to return to the Champions League on a stable basis and, if possible, reach the final sprint with a genuine chance of fighting for the title until the very last day. A Supercoppa win, especially against a coach like Conte, would be the perfect manifesto for the new Allegri era.
The stage makes the night even bigger: the match is played in a Final Four format, with the winner waiting for either Inter or Bologna in the final. A defeat would mean an early flight home and, above all, some psychological fallout ahead of the rest of the title race.
Allegri vs Conte: a clash between the Italian Maestri
The showdown between Milan and Napoli is inevitably also a duel between Massimiliano Allegri and Antonio Conte, both former Juventus coaches. Conte was the driving force behind Juve’s post-Calciopoli rebirth, won the Scudetto with Inter to break the Bianconeri’s dominance, and exported his aggressive 3-5-2 to the Premier League.
Allegri, for his part, has rewritten the manual on tactical versatility, switching smoothly from a back three to a back four, reaching two Champions League finals with Juventus and piling up domestic trophies in Italy.
In the past there has been no shortage of verbal sparks between these two masters, but in recent years mutual respect has come to the fore: both have acknowledged how much the other has helped raise the overall competitive level of Serie A.
From a tactical point of view, this Supercoppa offers a battle between two “cousin” 3-5-2 systems: Conte’s remains faithful to principles of intensity, pressing and attacking space with the mezzali, while Allegri’s version is more elastic, ready to morph into a 3-4-2-1 or 4-4-2 depending on the phase of play, with a strong focus on balance and the fine details that decide one-off games.
Pulisic, Modric and the Bartesaghi factor
Milan’s main attacking reference point is still Christian Pulisic. Since the American arrived in Serie A he has collected 41 goals and 22 assists in all competitions, including one against Napoli in the league meeting back in September. His recent brace versus Torino confirmed exactly why Allegri described him as “diabolical” in front of goal: few touches, almost always decisive.
In Saudi Arabia Pulisic is expected to start again in the front pairing alongside Christopher Nkunku, with Rafael Leão likely to be used only off the bench after travelling with the squad but still not being at 100% fitness.
The long absence of Santiago Gimenez – who will almost certainly need ankle surgery and faces at least six weeks on the sidelines – has reshuffled the hierarchy in attack, forcing Allegri to lean even more on the chemistry between Pulisic and Nkunku.
In midfield, the man running the show is still Luka Modric. At 40 years of age he continues to dictate the tempo, choosing when to speed the game up and when to slow it down. Around him move Ruben Loftus-Cheek, Adrien Rabiot and the runs of Saelemaekers and Bartesaghi down the flanks, in a 3-5-2 that on paper can easily become a 3-4-2-1, with Pulisic given more freedom to drift between the lines.
The real new factor is Davide Bartesaghi himself. The 2005-born left-sider, a product of the Rossoneri academy, enjoyed an almost surreal night against Sassuolo, scoring his first ever Serie A brace from the left wing-back position. His left foot and knack for attacking the far post make him a very interesting weapon in a tight, nervous game like a one-off semi-final on neutral ground. Allegri, who usually bloods youngsters step by step, seems ready to confirm him in the starting XI in Riyadh – a strong signal both to the player and to the rest of the dressing room.
At the back, the absence of Matteo Gabbia – left at home after a knee hyperextension – definitively opens up a place in the three-man defence for Koni De Winter, set to line up alongside Fikayo Tomori and Pavlovic in front of Mike Maignan.
Conte’s work between emergency and identity
Antonio Conte took over Napoli a few months after their Scudetto, following a very complicated season marked by coaching changes and a lost sense of identity. His mission was clear from day one: rebuild a recognisable, aggressive team, capable of defending high up the pitch and occupying the opposition box with structure and discipline.
Today Napoli present themselves with a well-oiled structure: Vanja Milinković-Savić in goal, a back three of Beukema, Rrahmani and Buongiorno, Giovanni Di Lorenzo wide on the right, a midfield run by Stanislav Lobotka with Scott McTominay and the young Gutiérrez completing the unit, and up front a dynamic trio of Lang, Neres and Højlund.
Kevin De Bruyne’s absence removes creativity and vision between the lines, but the arrival of McTominay has given Napoli a powerful box-to-box presence, strong in his timing of runs and able to turn defensive situations into attacking ones in just a few strides. Lobotka is back available and, for Conte’s football, that is almost like a new signing: the Slovak is the silent engine that allows the three centre-backs to remain aggressive without stretching the team too much.
In attack, Lang and Neres are tasked with compensating for the fact that Lukaku is still not ready to start. If the Belgian comes on during the game, the contest could change shape completely: there are very few defenders in the world who are happy to face him when fatigue starts to bite.
Head-to-head between Milan and Napoli: recent balance, longer Rossoneri history
Over the last 20 meetings there have been seven wins for Milan, seven for Napoli and six draws, with a slight tilt towards the Rossoneri in the more recent clashes. The freshest memory is the 2023 Champions League quarter-final, when Pioli’s Milan knocked out Luciano Spalletti’s Napoli by drawing 1–1 at the Maradona after a 1–0 win at San Siro. That tie became a kind of watershed: since then, every high-profile Napoli vs Milan has carried the echo of that European double header.
The most recent Serie A encounter this season also went Milan’s way, a 2–1 victory at San Siro inspired by a brilliant performance from Pulisic. It is on those positive sensations that Allegri will try to build his night in Riyadh.
Honours board of the Supercoppa Italiana
From 1988 to today, the Supercoppa Italiana has been won by a relatively small group of clubs, with a strong concentration among the northern giants. Juventus lead the honours board with nine titles, followed by Milan and Inter on seven, while Lazio have lifted the trophy five times. Napoli, thanks to their triumphs in 1990 and 2014, are now chasing a third success in this year’s edition. Roma, Parma and Fiorentina complete the picture with one Supercoppa each.
For Milan, a victory in Riyadh would mean drawing level with Juventus at the top of the all-time table on nine Supercoppe, confirming the Rossoneri’s extraordinary tradition in this competition.
Pre-match info
Match date and time (CET): Thursday 18 December 2025, 20:00 CET
Stadium: Al-Awwal Park, Riyadh (Saudi Arabia)
Referee: Luca Zufferli
Assistant referees: Imperiale, Rossi
Fourth official: Pezzuto
VAR: Aureliano
AVAR: Dionisi
Probable line-ups
Napoli
(3-5-2)
32 Vanja Milinković-Savić
22 Giovanni Di Lorenzo
13 Amir Rrahmani
4 Alessandro Buongiorno
21 Matteo Politano
68 Stanislav Lobotka
8 Scott McTominay
37 Leonardo Spinazzola
7 David Neres
20 Eljif Elmas
19 Rasmus Højlund
Team Manager 🧑🏫
Antonio Conte
Reserves 🔁
14 Contini (GK)
25 Ferrante
3 Gutierrez
5 Juan Jesus
31 Beukema
30 Mazzocchi
35 Marianucci
26 Vergara
69 Ambrosino
70 Lang
9 Lukaku
27 Lucca
Not available players ❌
Kevin De Bruyne (muscular injury – out)
Frank Anguissa (muscular problem – out)
Billy Gilmour (injury – out)
Alex Meret (hand injury – out)
Romelu Lukaku (returning from long lay-off – expected on the bench)
Milan 🔴⚫
(3-5-2)
Mike Maignan
Fikayo Tomori
Koni De Winter
Strahinja Pavlović
Alexis Saelemaekers
Ruben Loftus-Cheek
Luka Modrić
Adrien Rabiot
Davide Bartesaghi
Christopher Nkunku
Christian Pulisic
Team Manager 🧑🏫
Massimiliano Allegri