Greaves was signed by Italian Serie A club A.C. Milan in June 1961 for an £80,000 fee, and was given a three-year contract on £140 a week with a £15,000 signing bonus. He became unhappy at the thought of leaving London and tried to cancel the move before it was fully confirmed, but "Rossoneri" manager Giuseppe Viani refused to annul the deal. Greaves scored on his debut in a 2–2 draw with Botafogo at the San Siro. However, he did not get on well with new head coach Nereo Rocco, who insisted on keeping the players in a strict training regime with little personal freedom. Greaves scored nine goals in 14 appearances, including one against Inter Milan in the Milan derby. During a match against Sampdoria, Greaves kicked a player who had spat in his face. Sampdoria equalised from the resulting free kick, for which Rocco blamed Greaves, despite him having scored Milan's opener and set up the second. Due to his low morale, Greaves was transfer-listed and Brazilian attacker Dino Sani was signed as his replacement. Both Tottenham Hotspur and Chelsea made £96,500 bids, which were both accepted. After he left, the club went on to win the league title in 1961–62.