ROSSONERI SEEK CUP PROGRESS

Chris Lewis

22 Sep 2025 — 3 min read

Allegri's men take a break from league matters on Tuesday night, as Coppa Italia action takes centre stage at the San Siro. Fellow Serie A side Lecce are the visitors for this round two clash.

Match Details

Fixture: AC Milan vs Lecce
Date: Tuesday 23 September 2025
Kick-off: 21:00 local time at San Siro, Milan
Competition: Coppa Italia (Round 2)

Overview & Stakes

Milan host Lecce at San Siro, with a place in the Round of 16 up for grabs.
The Coppa Italia is one of Milan’s targets this season. The club came close last season (runners-up losing in the final to Bologna) and have not won the competition since 2003. Allegri is keen to end that drought. The competition offers a potential route into Europe - although the Rossoneri will be hoping to qualify for that via more conventional methods come the end of the season.
While Milan want to progress, this is an early round – which gives an opportunity to rotate the squad and give minutes to those less used. Maintaining freshness will be important given league commitments.

Recent Form & Psychological Edge

Milan have responded well since a surprise loss to Cremonese early in the Serie A campaign. They have won three consecutive league games: a 2-0 win away at tonight's opponents Lecce, 1-0 vs Bologna, and 3-0 vs Udinese.
That previous league win over Lecce gives Milan a psychological edge, knowing they can control the game vs this opponent - perhaps even more so being at the San Siro.
Lecce have been struggling lately. They are without a win in four Serie A matches, with draws or defeats, which adds pressure.

Team News & Possible Line-ups

Milan

Injuries / absences:

Rafael Leão remains out with a calf issue. He is expected to miss this match and possibly return for the next Serie A game.
Ardon Jashari is out until late October/November.
Mike Maignan could return between the sticks - though Allegri may not want to risk bringing him back too early with back-to-back fixtures against the league's current top two on the horizon.

Rotation & new names:

Christopher Nkunku, Milan’s summer signing, is in line for more minutes, possibly his first start. Allegri is likely to give fringe / newer players more opportunity in this match.
Defensive rotation expected: Koni De Winter may start in one of the centre-back positions alongside Tomori and Gabbia.
Midfield: players like Samuele Ricci and Ruben Loftus-Cheek could feature more, possibly in place of regular starters Modrić and Rabiot for parts of the game.

Possible line-up (Milan):

Terracciano; De Winter, Gabbia, Tomori; Saelemaekers, Loftus-Cheek, Ricci, Rabiot, Bartesaghi; Gimenez, Nkunku.

Tactical and Match Dynamics

What Milan will aim to do:

Control the tempo: Possession, especially in midfield, is key. With Rabiot still having a big influence, supplemented by Loftus-Cheek, Ricci, etc.., Milan should try to dominate the middle third and prevent Lecce from settling.
Use width: Players like Bartesaghi, Saelemaekers and Nkunku will be important to stretch Lecce’s defensive shape, opening gaps for midfield runners.
Integrate substitutes effectively: The game may not require full strength from minute one; Allegri might bring in more creative attackers, e.g. Pulisic, later on to unlock the game.
Clean defence early: Given Lecce will likely try to sit deep and counter-attack, Milan cannot afford lapses in the early stages. Rotated defence must stay compact.

What Lecce may try:

Defensive organization will matter; likely a more conservative setup, absorbing pressure and trying to hit on the break.
Target set-piece situations or transitional moments — Milan with rotated personnel might be vulnerable there.
Rely on individual moments from players such as former Milan loanee Riccardo Sottil, as well as other attacking outlets.

Key Players to Watch

Christian Pulisic: Already finding form. In the last game (versus Udinese) he scored twice and assisted once. Should he start, he could be dangerous especially in more open phases.
Christopher Nkunku: If he starts or plays a significant chunk, this is a chance for him to make an impression and establish rhythm. A goal would do him the world of good.
Rabiot / Loftus-Cheek: Their performance in midfield will determine whether Milan can dominate the game or be dragged into a more scrappy, transitional match.
Santiago Gimenez: Desperate for a goal and some good fortune. Will he get it here?

Predictions & Concerns

Likely result: Milan win, perhaps comfortably but not necessarily by a large margin. Many journalists expect a professional display culminating in a win by a two or three goal margin.
Goals-caveat: With rotation, there may be dips in intensity; Lecce might score, especially if Milan are less sharp in defence or misplace passes.
Risk: Squad depth will be tested. If Milan take the game lightly early, Lecce could exploit set-pieces or defensive miscommunication. Also, fatigue and focus will be something Milan need to manage given upcoming Serie A challenges. The next two league games are huge - with Napoli at home followed by Juventus away.