Milan – Napoli Serie A Matchday 5 September 28 2025 20:45CET
Milan is taking a solid shape with Allegri at the helm. Milan have not conceded a goal since the week 1 loss to Cremonese. The games have not been against the strongest opposition but the midfield has looked solid and the back three used have managed to keep the ball out of the net without looking spectacular.
The games will get tougher and a more telling run starts with this week 5 match versus Napoli. Between now and early November Milan will face Juventus, Fiorentina, Atalanta and Roma.
Leao is back in training and is ready for match action. The Portuguese might still be used as a sub only. Gimenez and Pulisic may be part of a 3-5-2 for one more week at least. The midfield is offering some options. The primary question mark is how much time is Loftus-Cheek going to get. The Englishman looked like a certain starter and he has backed it up so far but Allegri may prefer a middle five of Saelemaekers, Fofana, Modric, Rabiot and Estupinan. All five have looked good and solid providing energy, skill, leadership and more. Saelemaekers has even earned himself man of the match quality minutes. Modric is defying age questions and with a less than busy fixture list he has time for rest, as was the case in the Coppa Italia 3-0 win versus Lecce in midweek.
Tomori, Gabbia and Pavlovic have not impressed all that much. De Winter as back up hasn’t really gotten enough minutes so far. Yet, as mentioned, the team has looked solid so far. The initial three are set to keep their places but will a back three live for much longer.
Maignan came back from injury midweek but his longer term future as a Milan player continues to be questioned. Look for another possible and likely Bosman exit next summer.
Napoli have started the Serie A season with four wins in a row. However, an important player was added to their injured list. Alessandro Buongiorno is expected to miss a few weeks with an abductor injury. He is joined on the missing list with Romelu Lukaku. Rasmus Hojlund, widely linked to Milan over the summer, is expected to start again for Conte’s men.
Milan – Lecce Coppa Italia Matchday 3 September 23 2025 21:00CET
Off three Serie A clean sheets Milan face off with Lecce in the second of early Coppa Italia rounds. This early Coppa Italia participation was of course necessitated by losing to Bologna in last season’s final.
Logic would dictate that this is a time to give some regular players rest and save them for Napoli and the Serie A. The squad that is available for Allegri is not exactly full of options. De Winter and Odugu are the back central defender for example. Athekame, who had debut minutes during the weekend, is the back up right back and the Bartesaghi on the left. Ricci is the presumed central midfield back up and Jashari is unavailable due to injury at least until early November. Up front Leao is still not ready and aiming for the weekend with only Pulisic, Nkunku and Gimenez as options.
Perhaps all of the above supposed backup will get starting minutes but it feels like Nkunku is the most proven and the most likely to get the coach’s trust. Many feel that Gimenez needs to be given every chance to gain confidence and form, perhaps this might be his chance.
If Milan progress the next Coppa match will be against Lazio in December in the round of 16.
Udinese – Milan Serie A Matchday 4 September 20 2025 20:45CET
Week 3 versus Bologna featured a 1-0 win and another clean sheet. Allegri’s much discussed and criticized defensive shape was on view and at the very least has Milan with a questionable back line keeping the ball out of their own net. Starting all of Modric, Fofana, Rabiot and Loftus Cheek certainly overloads the midfield to add to what Allegri’s coaching is about. However, the game was tainted and marred by injuries and poor refereeing. The former had Pavlovic and Maignan exiting the game with what is now said to be minor injuries. The latter had referees not giving Milan two clear cut penalties. Even though the penalties were within the same sequence, as Nkunku was brought now twice in quick succession, Matteo Marcenaro in consultation with VAR Michael Fabbri dismissed the pleas. Allegri got himself red carded as the match concluded. After the match everyone up to Gabriele Gravina – the Italian football federation president – acknowledged the errors and Milan received an apology. The short term suspensions or ‘keep aways’ from games for the involved referees are not likely to rescue the current system where camera evidence is being brushed aside by several sets of eyes versus one set of eyes, as it was in the pre-VAR era.
Thankfully Modric had scored a great goal earlier in the match and Milan had the three points before the above farce. The aforementioned injuries force Allegri to use others from the thin squad at his disposal. Leao was hoped to be ready but he remains absent again and this probably means the 3-5-1-1 or 3-5-2 sees another light of day again. Allegri will eventually settle for a 4-3-3 or so we are led to believe.
Pulisic is reportedly ready for a start and is likely to start behind Gimenez. This looks to push Loftus-Cheek back into the midfield five. It is also possible that Gimenez starts on the bench with Pulisic further up. Fofana might be the player to give way if the expected tactics are chosen. Pavlovic could pass fitness tests and be ready to start, if not De Winter will take his place at the back. Tomori and Gabbia should continue to start from here to January, at least.
Pietro Terracciano will start in Maignan’s place. The Frenchman looks more and more like a Bosman exit next summer and his possible replacement will add to what can be another hectic summer next year.
Kosta Runjaic’s men have not lost yet this season. One of Udinese’s two wins this season include beating Inter 2-1 at the San Siro two weeks ago.
Milan – Bologna Serie A Matchday 3 September 14 2025 20:45CET
A Leao less Milan beat Lecce 2-0 away in week two for the first three points of the season. The game featured what could be called an unusual line up with Saelemaekers as a kind of a forward. His hard work only cemented the Belgian’s utility man tag. The game was an improvement over the week 1 loss versus Cremonese but Milan seem a long way off from a so called integrated team.
It was hoped that Leao will use the international break to get back to shape to play but this has not been the case and the Portuguese winger, now perhaps a forward, now aims to be ready for week 4 at Udinese. Nkunku is apparently not ready for starting 11 action either and this is already a case where this thin 22 man squad requires Allegri to be creative. Reports suggest a 3-5-1-1 is in the works. The sometimes maligned Gimenez ended up staying at Milan and his goals are now required even more. Loftus-Cheek scored the opener at Lecce and was mostly praised for his play. He is set to start behind the Mexican forward. The five man midfield survives and has more bodies for the middle three. Rabiot has joined Milan and welcomed as a familiar, experienced player for the middle. Ricci is therefore less likely to see minutes. Fofana and Modric will play alongside Rabiot. Estupinan and the aforementioned Saelemaekers will complete the midfield. The back three options are limited. De Winter may or may not get many minutes this season. For now Pavlovic, Gabbia and Tomori are likely to remain preferred.
There are already suggestions that the January transfer window will need to be used to add to the 22 squad size. There are also suggestions that Maignan could walk as a Bosman next summer leaving Milan with another move to make. This is in addition to the already needed steps for building a continually competing team, dealing with loans and more.
Bologna are of course the team that stood between Milan playing European football and not this season. Bologna’s win against Milan for the Coppa Italia title confined Milan to a relatively light schedule this season. Vincenzo Italiano’s team now includes Federico Bernardeschi and Ciro Immobile though the latter is out injured. This game is also drawing attention because Rabiot and Jonathan Rowe exited Marseille in the summer due to the two coming to blows in the dressing room. Rowe is a Bologna player now although he is likely to start on the bench.
Last season ended poorly of course, finishing eighth and missing out on European football was a blow to the team and its finances. Furlani’s claim that major sales are not needed was received skeptically and so it proved. Selling Reijnders to Manchester City for less than his perceived value was to start a typical yet overly chaotic summer transfer window.
Hiring Tare and a returning Allegri heralded a more normal period for Milan. The former an experienced sporting director and the latter an experienced coach should have resulted in a structured way of going about the summer business. Their past – in particular Allegri’s increasingly negative tactics – may not have been all what Milan fans wanted for the team now but the know how was needed to navigate yet another tweak or rebuild.
A prolonged player chase dominated most of the earlier parts of the transfer window and was reminiscent of the story of Charles De Ketelaere. Another Club Brugge player was coveted but his team were not budging and playing hard ball. Jashari eventually arrived – with a Milan fan tag attached to him – for the midfield.
Rumours aplenty as is normal for Milan and the likes of Ricci and Modric arrived to further bolster the midfield and provide much needed leadership. Theo’s poor form led to him seeking an exit and eventually accepting a Saudi League exit. A player who provided highlights earlier in his Milan career and had become a symbol of Maldini’s Milan left with more of whimper than anything else. Tare managed to gain some support for finding paid exit for Emerson Royal and a relatively large profit for Thiaw.
As the season started poorly with a loss to Cremonese and the squad thinner problems and questions started to pile up again. Exit rumours exploded and started to materialize with the likes of Okafor leaving Milan and leaving the team with fewer options. A 3-5-2 was all but forced on Allegri and this led to a team with Leao and Pulisic on the front lines and Gimenez unwanted and/or in poor form subbing and contemplating an exit.
Right back had become a weak point and the departure of Theo had added urgency for the other side of the pitch. Several less than exciting names were rumoured. Milan settled on Estupinan for the left back and Athekame for the right back. At least the former was experienced and defensively capable. The latter was a young project type player. This further forced Allegri into improvising and using the likes of Saelemaekers.
Camarda followed many more young players out the door with buy back clauses seen as a positive. A team with little offensive bodies was adding questions for itself and instead looking at not so cheap players like Conrad Harder. All the while the long rumoured Vlahovic pursuit popped up and faded back down.
As the summer transfer window reached its deadline climax the ‘Allegri needs players’ phrase popped up more and more as the coach seemed unsure what formation he should or could use. The number of players allowed to leaved accelerated to the point of leaving the team with barely a backup. Some agreed that so called deadwood should be disposed of but was it all too much. By the end of it all 17 members of the team ended the 2024-2025 season beating Monza 2-0 had departed. Some left on loan with a good chance of returning next summer, of course.
The list is indeed long and shown in the graphic above. All of Reijnders, Thiaw, Henandez, Emerson Royal, Musah, Jimenez, Sportiello, Bondo, Filippo Terracciano, Jovic, Chukwueze, Camarda, Florenzi, Felix, Abraham, Sottil and Walker left Milan. They were joined by others who were on loan and exited again. These were Okafor, Colombo, Morata, Lazetic, Vasquez, Calabria, Pobega and Pellegrino.
The full incoming or replacements list is Modric, Ricci, Jashari, Estupinan, Pietro Terracciano, De Winter, Athekame, Rabiot, Nkunku and Odogu. This ends up with the team being 22 man strong. Not many would agree that this is enough, even without the rigours of European football. In euros the incoming and outgoing amounts are very close. A tally counting all reported full transfer and loan fees has the team almost even and saving a bit more in salary.
Nkunku’s somewhat surprising fast moving and full transfer from Chelsea could be the wild card for a team lacking depth up front. Even if Allegri might need some thinking in using the Frenchman well. The midfield is surely the strength of the team but the same could not be said for the defense. Very early signs do not bode well with Tomori, Pavlovic and Gabbia not standing out in the first two Serie A games so far. De Winter and the late arriving prospect Odogu provide cover but will need to show if they are capable.
A year zero might have been expected after the failures of last season but barring a great rebound another might be expected and it can lead to another chaotic big headache for all involved.
Adrien Rabiot has joined Milan in what is a last minute signing for a player Allegri knows and likes. The midfield is one position that most would agree has been strengthened with the likes of Modric, Jashari and Ricci joining Fofana, Loftus-Cheek. Rabiot adds further strength with the departures of the likes of Musah opening up a spot for another player.
The 30 year old Frenchman, formerly at Juventus, joins from Marseille after being involved in a dressing room fight with now former team mate Jonathan Rowe. Both player have been exiled from Southern France and as fate would have it are set to face each other during the week 3 match versus Bologna.
The reported transfer fee is around €10 million on a €5 million salary. Rabiot has signed for three years until June 2028.
