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AC Milan Season Preview: 2023/24

Milan are coming in with a very different squad and it ll comes down to how quickly they adapt with a difficult opening ten games.

AC Milan v FC Barcelona - Preseason Friendly Photo by Claudio Villa/AC Milan via Getty Images

AC Milan are coming off a complicated season and tumultuous start to the summer. Milan had a mixed bag of results last season with a deep run in the Champions League but a huge drop off in Serie A with the side just sneaking into the top four. The summer started with club legend Paolo Maldini leaving as Technical Director alongside Ricky Massara with the sporting decisions falling under CEO Giorgio Furlani going forward supported by Moncada and D’Ottavio. The rest of the summer brought a huge shake up as Sandro Tonali was sold followed by eight purchases to transform the attack and midfield. Stefano Pioli remains being his side is completely different and will have to gel right off the bat given how difficult their opening ten games are going to be. There are questions around the 4-3-3 or 4-2-3-1 formations as both have pros and cons but the biggest gap is the lack of a defensive minded midfielder and the lack of depth at centre back. Here’s a breakdown of the side and what to expect:


Starting with the keepers, Mike Maignan is the best by a mile in the league but he needs to keep fit and play the whole season as we need him this year. We threw away our competitiveness last year in the stretch where he was missing and Ciprian Tatarusanu was filling in. The addition of Marco Sportiello is a good upgrade but he has made some fumbles in pre-season. He is a big upgrade on Tata and should be able to step in sufficiently.

We are light at centre back as Matteo Gabbia is out on loan and Simon Kjaer looks out of it. Fikayo Tomori and Malick Thiaw are the clear favourites to start with Pierre Kalulu their first back up but the depth is lacking. Tomori is looking rusty while Thiaw is still raw, they need to build some chemistry and to be in tune with the games with fewer drops in concentration. It seems Milan will add a player to this department but the deal is not yet closed.

We seem solid at right back as Davide Calabria is back from injury and looked good in the final friendly of the summer. He has Alessandro Florenzi and Pierre Kalulu waiting as his cover. Theo Hernandez is now the vice captain and will be holding down that spot but likely with a more defensive outlook given the changing face of the midfield. It is unclear if Fode Ballo-Toure will be his backup for the season or not as the Senegal international is expected to leave he club.

As a note, the defence is definitely weaker as the core defensive midfielder has left for the second summer in a row. We lost Franck Kessie in 2022 and now Sandro Tonali in 2023 without replacements while Ismael Bennacer is injured and will likely only return in early 2024.


The midfield is where we have the biggest shake up this summer. Tonali has left while Bennacer is injured so the starters from last season are out. Pioli is not set on a 2 or 3 man midfield yet. Regardless, we can assume that Ruben Loftus-Cheek and Tijjani Reijnders are the first names on the list to occupy spots before Rade Krunic fills in the defensive role. Loftus-Cheek is easily the best performer from the pre-season showing promising signs while I am tipping Reijnders to be our breakout star for the season. The midfield is compelling but imbalanced as the players in there are attack minded but do not cover enough ground for Pioli’s press and cannot effectively cover the defensive as a additional line.

Luka Romero is another exciting prospect from the market but it remains to be seen how often he will be used or if he goes out on loan. Yacine Adli is a huge question mark as he looks brilliant when he features but still is not getting any faith from Pioli, he is likely to leave but could play a role in the side. Yunus Musah is another potentially big summer signing but this all depends on hwo Pioli deploys him for the season, if he is converted into a CDM or plays a box-to-box role or if he pretty much sits on the bench except for rotations. Finally, Tommaso Pobega rounds out the depth but he will likely see less playing time given the increased competition for places.

The midfield is the make or break part of the field this year. If the midfield works, the attack is flowing and there is defensive cover, Milan can challenge for the title. but if the struggle to adapt and keep getting caught out, the Rossoneri will struggle to be in the top four. This midfield revolution will dictate the outcome of the season for us.


This is the first summer in about a decade where Milan have made crucial upgrades in the attack specifically to the right wing. The attack is carrying the bulk of the excitement with the arrivals of Samuel Chukwueze, Noah Okafor and Christian Pulisic. Once again, it depends if Pioli plays a 4-3-3 or a 4-2-3-1 as this dictates whether Chukwueze and Pulisic will be competing for a spot or starting together. Rafael Leao will occupy the starting left spot in either line up and will be happy to have players who can dribble in the middle and on the right to take off some pressure from him and open more spaces. The attack is much better than the previous two seasons and we should be aiming to boost our goal output by at least 10-15.

Olivier Giroud should start as the striker but should be heavily rotated with Okafor as the Swiss striker offers pace and ability to dribble while Giroud is often static. Giroud should play against the sides who defend deep while Okafor fits best for free flowing sides. The depth here will depend on the final days of the market as Marko Lazetic and Lorenzo Colombo are expected to leave on loan while it is not certain whether Divock Origi leaves this summer or if he is in the plans if he remains. Furthermore, Alexis Saelemaekers is expected to leave following in the footsteps of Junior Messias.

The attack looks great but there are injury concerns for Okafor and Pulisic thus it seems smart to either sign a young striker or keep one of Colombo, Lazetic and Origi around. The multiple options on the wings is exciting and the competition for places should fuel good performances from the attackers. The big hope is obviously nhot to have any of the players totally flop as Charles de Ketelaere did last summer as that will upend the season.

Serie A Position: 4

Champions League stage: Quarter finals

Coppa Italia: Champions

Top Scorer: Rafael Leao

Most Assists: Samuel Chukwueze

Best Player: Ruben Loftus-Cheek

Breakout Star: Tijjani Reijnders

Best New Signing: Samuel Chukwueze

Dark Horse: Pierre Kalulu and Yacine Adli

Overall Prediction

I have two likely outcomes depending on the first ten matchdays. Milan will either fight for the title and finish in 1st or 2nd place or the side will struggle to function with all the new faces and struggle to string wins together resulting in the team just scraping into 4th place or more likely finishing 5th for the Europa League. Milan’s stability heading into last season is what allowed them to be in second place at the midway point of the season, now Juventus and Inter Milan have that advantage.

The top four fight is crazy this season and it will be a tough ask for Pioli to maintain consistency and deliver Champions League football again. Napoli, Lazio and Inter are some of the strongest teams coming into the season. Juventus only have domestic competitions while AS Roma have reinforced significantly over the summer. The dark horse will be Atalanta who have cleaned house and have an entirely new look with a solid attack. Furthermore, sides like Fiorentina and AC Monza will be looking to cause some upsets and throw the top of the table into chaos whenever they get the chance.

Milan have a tougher Coppa Italia bracket compared to last year so let’s hope it is taken seriously and we don’t get knocked out in the first round. I sincerely believe Pioli should prioritise the tournament to add some silverware and give the side knock out experience. This is an opportunity for some silverware that we haven’t won since 2003 and is overdue.

The difficult prediction is for the Champions League where I believe the Rossoneri will do well as the team has good experience now but will not go as far as last season. Milan will have to rotate well and secure the next round sooner rather than later to be able to make a push for the top four or the title in January/February where the side slipped up last season.

As a note, it is likely we see Milan win something or this is Pioli’s final season in charge. Given the management shake up, it seems likely that another average season will not be tolerated especially if he is not nurturing the young talent or overly relying on his rigid system and older favourites.


Where Will AC Milan Finish In Serie A?

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  • 43%
    (29 votes)
  • 50%
    2-4 (UCL Places)
    (33 votes)
  • 6%
    5-7 (UEL/UECL Places)
    (4 votes)
  • 0%
    8 and below
    (0 votes)
66 votes total Vote Now