On 27 July 2017, he was featured in the starting line-up for the first time in a 1–0 away victory over Romanian side Universitatea Craiova in the 2017–18 Europa League qualification. On 3 August, he scored his first goal for Milan in the return match of the same tie, which finished 2–0 for his team. On 20 August, he scored his first Serie A goal in a 0–3 Serie A away win against Crotone. On 24 August, he scored the only goal in a 1–0 away victory over Shkëndija in Europa League play offs, and on 28 September, he scored a last-minute winning goal against Rijeka in the group stage to win the match 3–2 for Milan. Coming on as a substitute in the Coppa Italia match against local rivals, Internazionale, Cutrone scored the winner and his first goal in the Derby della Madonnina.