Milan hit rock bottom last season, slumping to their lowest Serie A finish in a decade despite significant spending. After two Portuguese coaches failed to meet expectations, the San Siro giants have ...
Milan hit rock bottom last season, slumping to their lowest Serie A finish in a decade despite significant spending. After two Portuguese coaches failed to meet expectations, the San Siro giants have turned to a familiar face to restore stability and reverse their fortunes.
Eleven years after leaving the club for Juventus, Massimiliano Allegri returns to his old stomping ground to help Milan rebuild from scratch. Indeed, the 58-year-old won his first Scudetto at San Siro before establishing a dynasty in Turin. However, Allegri’s second stint at the Allianz Stadium didn’t go well.
The experienced tactician must roll back the years to help Milan dig themselves out of the hole. A 2-0 win over Bari in the opening Coppa Italia round was a perfect way to announce his return. Yet, Serie A is a different type of challenge, and another season without Champions League football would be a disaster.
Competition is as fierce as it gets as we look at our Milan season preview for 2025/26.
Milan Fixtures
Milan’s league campaign kicks off on home turf against newly-promoted Cremonese on Saturday. Their first away game of the season pits them against perennial bottom-half strugglers Lecce in round two. As such, a strong start to Allegri’s second tenure at San Siro seems like a distinct possibility.
The first high-profile match arrives at the end of September as Milan entertain reigning title holders Napoli on home soil. That fixture serves to get a rough patch underway, with the Rossoneri taking on arch-rivals Juventus on the road in the following round.
Then, they face Fiorentina (H), Pisa (H), Atalanta (A), and Roma (H) in quick succession. The first edition of the famous Derby della Madonnina of the 2025/26 campaign takes place on November 23, with Inter ‘hosting’ Milan at San Siro. The eternal rivals renew hostilities in the reverse fixture in early March.
Milan close out the calendar year at home against Hellas Verona and head to Sardinia to meet Cagliari at the start of 2025. Interestingly, the reverse clash against the Islanders serves to drop the curtain on their 2025/26 season.
Transfer Business
It’s been a transitional summer for the seven-time European champions. A lack of Champions League football saw Milan part ways with two elite first-team stars. Indeed, Tijjani Reijnders has joined Manchester City in a mega-money deal, while Theo Hernandez left Europe to sign for Saudi Pro League heavyweights Al-Hilal.
Malick Thiaw’s transfer to Newcastle United marks another high-profile departure. Other outgoing deals include Emerson Royal’s move to Flamengo and Marco Pellegrino’s switch to Boca Juniors. Milan have also loaned out several fringe players, including Tommaso Pobega, Warren Bondo, and Filippo Terracciano.
After failing to earn new contracts, Luka Jovic and Davide Calabria severed ties with the club. Forced to plug significant gaps within the squad, Milan have been equally active on the incoming front.
Italian star Samuele Ricci has arrived from Torino to fill Reijnders’ shoes, with Ardon Jashari joining the team from Club Brugge after a month-long saga. Let’s not forget that Luka Modric has penned a short-term contract, with the former Ballon d’Or winner expected to bring experience and much-needed winning mentality.
Meanwhile, Milan have landed Pervis Estupinan from Brighton to replace Hernandez and Koni De Winter to take Thiaw’s place in defense. Zachary Athekame has swapped Young Boys for San Siro to increase competition on the flank. Furthermore, Milan are on the verge of signing Victor Boniface from Bayer Leverkusen on loan with an option to buy to boost Allegri’s attacking options after Alvaro Morata joined Como.
Starting Line-up
Milan will, in all likelihood, line up in a 3-5-2. It’s the same formation Sergio Conceicao used toward the end of last season. However, Allegri has achieved greatness relying on this set-up, so he intends to stick with it as the foundation of his new Rossoneri project.
Despite strong links with Chelsea, Mike Maignan remains at Milan and continues as their first-choice goalkeeper. In defense, De Winter could slot in next to Strahinja Pavlovic and Fikayo Tomori, perhaps at the expense of Matteo Gabbia.
Estupinan should be the first choice on the left wing, with Alexis Saelemaekers expected to operate on the opposite flank. Ricci will likely be the new mainstay in the engine room. Youssouf Fofana should have a guaranteed starting berth alongside the ex-Torino ace, with Ruben Loftus-Cheek the likeliest candidate to complete the midfield trio.
Boniface’s arrival could trigger further changes in the final third. Yet, Rafael Leao and Christian Pulisic are the favorites to spearhead Milan’s attack this season. After an unimpressive half-season in Serie A, Santiago Gimenez has dropped to the bench.
Prediction
It will be exciting to see how Allegri reshapes Milan in his second stint, especially with so many fresh faces and key departures. The Rossoneri boast enough quality to fight for a top-four finish.
However, much will depend on how quickly the new signings adapt and whether Allegri can rediscover the winning formula that once made him one of Italy’s most successful coaches.
A return to the Champions League looks like a realistic target, though mounting a serious Scudetto challenge may take at least another year of rebuilding.
Category: General Sports
