On 28 June 2016, Milan announced Montella as their new head coach with a contract starting from 1 July. He signed a two-year deal, reportedly worth €2.3 million per year, while Sampdoria was paid €500,000 as a compensation to release him from his contract. On 23 December, Montella led the "Rossoneri" to their first title since 2011, the Supercoppa Italiana, defeating Juventus 4–3 in a penalty shootout after a 1–1 draw following extra time. With a 6th-place finish in the league his first season as the club's head coach, Montella led Milan to qualify for the 3rd round of 2017–18 UEFA Europa League qualification phase, marking Milan's return to European competition for the first time since February 2014. On 30 May 2017, he signed a new contract until 2019.