Rubuta ci gaba don wannan sakin layi - A ranar 6 ga Yuli, 2009, yayin da ƙungiyar Milan ta sake haɗuwa don horar da kakar wasa, an nada Ambrosini a matsayin kyaftin din kulob din, wanda ya gaji abin wuya 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 a kakar wasa ta 2011-12
da ficewar manyan 'yan wasa Filippo Inzaghi, Alessandro Nesta, Gennaro Gattuso, da Clarence Seedorf, An ba da rahoton cewa Ambrosini yana la'akari da makomar sa tare da kulob din, amma Adriano Galliani ya sami damar 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.