Montella began his managerial career as Roma's caretaker manager in 2011, later coaching Catania the following season. In 2012, he moved to Fiorentina, where he spent three seasons, leading the club to three consecutive fourth-place league finishes, the 2014 Coppa Italia final and the UEFA Europa League semi-finals in 2015. After a season-long spell with Sampdoria, he was appointed Milan's manager in 2016, and later that year, he won his first title as a coach with the club, the Supercoppa Italiana. He was sacked by the club in 2017 and was subsequently appointed the new manager of Spanish side Sevilla. Despite reaching the Copa del Rey final and reaching the Champions League quarter-finals for the first time in the club's history, he was sacked by Sevilla 4 months after his appointment following a run that included nine matches without a victory. He returned to Fiorentina in 2019, with the second spell lasting over 8 months.