Nyorai mberi kweiyi ndima - Mushure mekugara kwake neJuventus, Rossi akaenda kuMilan yaitambura panguva iyoyo kwemwaka muna 1985. Munguva yake neMilan, akayeukwa nekuda kwezvinangwa zviviri zvaakarova achipesana neInternazionale mumutambo weMilan derby. Rossi akasarudzwawo muchikwata cheItaly che 1986 FIFA World Cup kuMexico, asi haana kutamba mumakwikwi; kukuvara kwakamuita kuti atambure panguva yekuyedzwa kwechikwata, nekuda kwekukwirira kwenzvimbo iyi. Somugumisiro, akatsiviwa naGiuseppe Galderisi kumusoro-mberi muboka rekutanga. Akaita chitarisiko chake chekupedzisira kuItaly musi wa11 Chivabvu 1986, mukukunda 2-0 pamba neChina muNaples. Akapedza basa rake rekirabhu kuHellas Verona mumwaka wa1986/87.
mwaka, achivabatsira kuti vapedze vari pachinzvimbo chechina muSerie A, vasati vaenda pamudyandigere pakupera kwemwaka. Akanga achibatanidzwa muzvivako, pamwe chete neaichimbova mutambi wake Giancarlo Salvi.