Buuxi weedha soo socota: Bishii Luulyo 6, 2009, markii kooxda Milan ay dib isugu soo laabteen tababarka xilli-ciyaareedka ka hor, Ambrosini waxaa si rasmi ah loogu magacaabay kabtanka kooxda, isagoo dhaxlay suunka gacanta ee Paolo Maldini. Bishii Sebtember 8, 2009, wuxuu ku daray hal sano oo kale qandaraaskiisa, isagoo sii waday joogitaankiisa kooxda ugu yaraan illaa 2011. Wuxuu ku guuleystay horyaalka Serie A xilli ciyaareedkii 2010-11 isagoo leh seddex ciyaarood oo gacanta ah, isagoo ka adkaaday kooxda ay xafiiltamaan ee Internazionale. 19kii Maajo 2011, wuxuu saxiixay heshiis cusub oo hal sano ah. Kadib markii uu ku soo dhamaaday kaalinta labaad ee tartanka
Xilli ciyaareedkii 2011-12 iyo bixitaanka ciyaartoyda kale ee Filippo Inzaghi, Alessandro Nesta, Gennaro Gattuso, iyo Clarence Seedorf, Ambrosini waxaa lagu soo warramey inuu ka fiirsanayo mustaqbalkiisa kooxda, laakiin Adriano Galliani wuxuu ku qancay Massimo inuu saxiixo heshiis kale oo hal sano ah oo uu sii wado inuu kabtan u noqdo Milan xilli ciyaareedka 2012-13. Ka dib bilow aad u adag oo leh guul darrooyin dhowr ah oo cajiib ah, Milan ayaa ugu dambeyntii ku dhameysatay xilli ciyaareedkii kaalinta saddexaad ee ka dambeysa horyaalka Juventus iyo kaalinta labaad ee Napoli, iyagoo xaqiijiyey booska wareega isreebreebka ee Champions League xilli ciyaareedka soo socda.