 Ramba uchiverenga ndima ino - Ambrosini akatanga basa rake neCesena uye akapedza kudzidza kuchikwata chavo chekutanga aine makore gumi nemanomwe panguva yemwaka wa1994-95. Murairidzi weAC Milan Fabio Capello akabva akunda mujaho wekumutora gore rakatevera, uye kunyangwe akatarisana nemakwikwi akaomarara kuti apinde muchikwata chenyeredzi dzeMilan, Ambrosini akapihwa mitambo mishoma apo timu yakakwikwidza kumakwikwi eSerie A. Yakashandiswa mumwaka wa1996-97 nguva nenguva chete, Ambrosini akatumirwa nechikwereti kuVicenza, kwaakapihwa nzvimbo muchikwata chekutanga chinenge pakarepo, uye akabatsira timu yake kudzivirira kudzikiswa pakupera kwemwaka. Akasvikawo kuma semi-fainari eEFAFA Cup Winners Cup naVicenza. Akadanwa kuSan Siro, Ambrosini pakupedzisira akaita nzvimbo yechikwata chekutanga sezvo Milan yakakunda zvakare mukwikwidzi weSerie A muna 1999. Anogara achitevera, akaona mikana yake yakaganhurirwa nekukuvara kwemabvi kunonetsa asati adzokera pakugwinya kuzere kubatsira Milan kuhwina Coppa Italia kurova mukukunda 4-1 mumutambo wekutanga wekupedzisira pamusoro peRoma uye UEFA Champions League mumwaka wa2002-03, kwaakatsiva Rui Costa muminiti yechi87 yekupedzisira vachipesana neJuventus, yakaitirwa kuOld Trafford. 