Kammala jumla mai zuwa: A ranar 6 ga Yuli, 2009, yayin da kungiyar Milan ta sake haduwa don horar da kakar wasa, an nada Ambrosini a matsayin kyaftin din kungiyar, inda ya gaji belin daga Paolo Maldini. A ranar 8 ga Satumba, 2009, ya kara shekara guda a kwantiraginsa, ya tsawaita zamansa tare da kungiyar a kalla har zuwa 2011. Ya lashe taken Serie A a cikin kakar 2010-11 tare da wasanni uku a hannu, yana fitar da abokan hamayyar birnin Internazionale. A ranar 19 ga Mayu 2011, ya sanya hannu kan sabon kwangila na shekara guda. Bayan wani abin takaici na biyu gama a cikin
Lokacin 2011-12 da kuma ficewar manyan 'yan wasa Filippo Inzaghi, Alessandro Nesta, Gennaro Gattuso, da Clarence Seedorf, An ba da rahoton Ambrosini yana la'akari da makomar sa tare da kulob din, amma Adriano Galliani ya iya shawo kan Massimo ya sanya hannu kan wata yarjejeniyar shekara guda kuma ya ci gaba da kasancewa kyaftin din Milan a kakar 2012-13. Bayan farawa mai wahala tare da shan kashi da yawa, Milan daga karshe ta kammala kakar wasa a matsayi na uku a bayan masu kare kambun Juventus da masu tsere Napoli, inda suka samu gurbi a wasannin neman shiga gasar zakarun Turai na kakar wasa mai zuwa.