The following season, Milani made his Serie A debut with Sampdoria during the 1958–59 Serie A season, on 21 September 1958 in a 1–0 defeat against Lazio, in Rome. He formed a formidable attacking trio with Mora and Cucchiaroni throughout his first season, scoring 13 goals. During the 1959–60 Serie A season, however, he was injured to his leg in a match against Bologna, which prevented him from playing for a lengthy period.