2018–19 A.C. Milan season
Date Pos Player A Moving to Fee Notes
29 January 2019 MF Nicola Torchio 18 Brescia Undisclosed From Primavera team
29 January 2019 FW Jacopo Finessi 18 Padova Undisclosed From Primavera team
31 January 2019 DF Raoul Bellanova 18 Bordeaux €1,000,000 From Primavera team
1 February 2019 MF Sergio Sanchez Gioya 19 Leganés Undisclosed From Primavera team
5 February 2019 GK Alessandro Guarnone 19 Chiasso Undisclosed After anticipated return from loan
15 February 2019 MF Mattia El Hilali 21 Chiasso Undisclosed After anticipated return from loan
Transfers -- Winter window
The 2018-19 season was the 120th season in Associazione Calcio Milan's history and their 85th (108th overall) in the top-flight of Italian football. Milan competed in Serie A, the Coppa Italia, the UEFA Europa League and the Supercoppa Italiana. Milan qualified for the 2018-19 UEFA Europa League group stage as the sixth-placed team of the previous season, but were originally banned by UEFA from European competition due to violations of Financial Fair Play regulations for failure to break-even. On , Li Yonghong failed to keep up with his loan repayment plan, neglecting to deposit a €32 million installment on time in order to keep refinancing the €303 million loan debt owed to Elliott Management Corporation. As a result, ownership of the club was immediately transferred to the American hedge fund. Milan appealed to the Court of Arbitration for Sport, and the ban was overturned on . Following the shareholders' meeting held on , all previous directors, including Marco Fassone and Massimiliano Mirabelli, were officially dismissed, with Paolo Scaroni becoming the new chairman of the club, replacing Li Yonghong. In the summer of 2018, Leonardo returned to Milan as a sporting director, while the club's hall of fame player Paolo Maldini was hired for the first time as a sporting strategy and development director. In September 2018, the club hired a new CEO, Ivan Gazidis, who had previously worked with Arsenal for over a decade and began his work with Milan on 1 December 2018. Once again, the club failed to achieve its primary objective of qualifying for the Champions League, either through winning the Europa League (Milan suffered a group stage elimination), or finishing in the top 4 of the national league competition, i.e. Serie A. On 28 May 2019, following an unsatisfactory result, both Leonardo and Gennaro Gattuso announced their resignations, with the latter donating his entire €5,5 million severance package back to the club.