Kammala jumla mai zuwa: Bayan shekaru takwas masu nasara a Peñarol a cikin wasansa na Uruguay, kungiyar Serie A ta Italiya A.C. Milan ta sayi Schiaffino, a lokacin da aka ba da lambar yabo ta duniya na Lire miliyan 52, a watan Satumbar 1954. Ya buga wasanni 171 tare da A.C. Milan kuma ya zira kwallaye 60, kuma ya halarci wasan karshe na gasar cin kofin zakarun Turai na 1958, wanda Milan ta yi rashin nasara a hannun Real Madrid 2<unk>3 (aet). Ya kasance daga cikin mahimman 'yan wasan da ke kai hare-hare a cikin ƙungiyar Milan wacce ta mamaye taurari na ƙasashen waje kamar Nils Liedholm da Gunnar Nordahl. Schiaffino ya lashe gasar zakarun kasa uku tare da Milan, nasarar da aka samu a 1955, 1957 da
Shekara ta 1959. Schiaffino ya bar 1960 don shiga Roma, inda ya taka rawar gani a cikin shekaru biyu masu nasara, wanda Roma ya gama na biyar a cikin matsayi.