Milan would have also qualified for the UEFA Europa League but was later excluded due to financial fair play issues.

[7][8] On 8 October 2019, Milan dismissed coach Marco Giampaolo (due to poor results) after only 3 months of employment.

[9] On 7 March 2020, it was announced that the contract with the club's "Chief Football Officer" Zvonimir Boban had been terminated.

[9] A week prior to his dismissal, Boban was interviewed by La Gazzetta dello Sport and criticized the club's CEO Ivan Gazidis over rumors involving him signing a secret pre-contract deal with football manager Ralf Rangnick for the following season.

[10][11] After Boban's dismissal was officialized, the club's chairman Paolo Scaroni stated his support of Gazidis.