Kutevera makore ake masere akabudirira muPeñarol mumutambo wake wekuUruguay, Schiaffino akatengwa neItaly Serie A kirabhu A.C. Milan, panguva iyoyo mari yepasi rose yemamiriyoni makumi mashanu nemashanu emadhora, munaGunyana 1954. Akatamba mitambo 171 neA.C. Milan uye akarova zvibodzwa makumi matanhatu, uye akapinda mu1958 European Cup Final, iyo Milan yakarasikirwa neReal Madrid 2<unk>3 (aet). Akanga ari pakati pevatambi vakakosha vekurwisa muchikwata cheMilan chaitongwa nenyeredzi dzekunze dzakadai saNils Liedholm naGunnar Nordahl. Schiaffino akakunda mikombe mitatu yenyika neMilan, kukunda kuri muna 1955, 1957 na1959
. Schiaffino akasiya muna 1960 kuti ajoine Roma, kwaakatamba basa rake mumwaka miviri yakabudirira, umo Roma yakapedza yechishanu mumakwikwi.