 Montella akatanga basa rake semutungamiri weRoma mu2011, akazotungamira Catania mwaka wakatevera. Muna 2012, akatamira kuFiorentina, kwaakagara mwaka mitatu, achitungamira kirabhu kunzvimbo nhatu dzinoteedzana dzechina muligi, 2014 Coppa Italia yekupedzisira uye UEFA Europa League semi-fainari muna 2015. Mushure memwaka-wakareba neSampdoria, akagadzwa maneja weMilan muna 2016, uye gare gare gore iro, akahwina zita rake rekutanga semurairidzi nekirabhu, iyo Supercoppa Italiana.. Akadzingwa nekirabhu muna 2017 uye akazogadzwa maneja mutsva wechikwata cheSpanish Sevilla. Pasinei nekusvika kuCopa del Rey yekupedzisira uye kusvika kuChampions League quarter-fainari kekutanga munhoroondo yekirabhu, akadzingwa neSevilla mwedzi mina mushure mekugadzwa kwake zvichitevera kumhanya kwaisanganisira mitambo mipfumbamwe isina kukunda. Akadzokera kuFiorentina mu2019, aine chiperengo chechipiri chakatora anopfuura mwedzi misere. 