 Nyora kupfuurira kweiyi ndima - Mutambi ane hunyanzvi uye anogadzira, Montolivo akatanga basa rake neAtalanta muna 2003 asati ajoina Fiorentina muna 2005. Akaenderera mberi kuita zvinopfuura 250 kuoneka kwekirabhu mumakore manomwe. Muna 2012, akasaina kuMilan pane yekuchinjisa yemahara uye, zvichitevera kuenda kwaMassimo Ambrosini, akashanda semutungamiriri wechikwata kubva muna 2013 kusvika 2017, kuhwina 2016 Supercoppa Italiana. Akasiya kirabhu muzhizha ra2019, asati aenda pamudyandigere gore iro. 