 Nyorai mberi kweiyi ndima - Akazvarwa muPadua, Veneto, Bortolotto akatanga basa rake kuCalcio Padova, ndokuzobatana neA.C. Milan timu yevechidiki. Mumwaka wa2002-03, akatamba mutambo wake wekutanga weSerie A wechikwata chevakuru, mutambo wechitatu wekupedzisira wemwaka, pamberi pe2003 UEFA Champions League Finaluye 2003 Coppa Italia Final. Milan yakazorora inenge yose yevatambi vavo vanotanga panguva yemutambo, uye yakashandisa 11 Primavera Team vatambi pamunda uye pabhenji. Bortolotto akatsiva Alessandro Matri muminiti yechimakumi manomwe nerimwe; mutambo wakapera mukurasikirwa kwe4 × 2 kumba kuPiacenza. 