Massimiliano Allegri was dismissed by AC Milan on May 26, 2026, after just one season in charge, following the club's failure to secure a spot in the Champions League [1, 2].
Allegri had returned to Milan in May 2025 after a year out of football, tasked with revitalizing a team under new ownership by RedBird Capital Partners that had limited recent success despite winning the Serie A title in 2022 [1, 2]. Milan finished the previous season in 8th place, missing out on European competition [1, 2].
The 2025-26 season began poorly with a 2-1 loss to Cremonese but improved as Milan went on a 24-game unbeaten league run before ultimately being overtaken by bitter city rivals Inter Milan [1, 2]. However, Milan still failed to qualify for the Champions League.
This outcome fell short of the expectations placed on Allegri, who had previously won the Serie A with Milan in 2011 during his first spell at the club [1, 2]. His coaching career also includes two spells at Juventus, where he won five Serie A titles and four Coppa Italia trophies during his first tenure, although he never captured the Champions League despite reaching two finals. His second Juventus stint lasted three seasons, yielding only one Coppa Italia win before his dismissal [1, 2].
Allegri's coaching style, often described as patient and conservative, has divided fans but was generally accepted when producing trophies [1, 2]. Milan's limited success under RedBird ownership has included only an Italian Super Cup last season, falling short of league or European ambitions [1, 2].
The club’s decision to part ways with Allegri closes this chapter, leaving Milan to search for a new head coach ahead of the next season.