In the summer of 2018, Milan's new board of directors decided to increase the team's attacking capability with the signing of a high-profile goalscorer, Gonzalo Higuaín, whom Cutrone first met in 2015 as a fan. Following his arrival, out of all the remaining strikers in the team (namely Nikola Kalinić, André Silva, and Carlos Bacca), Cutrone was the only one to have not been placed on the transfer market. On 31 August 2018, Cutrone came on as a late substitute and scored a last-minute match-winning goal in a 2018–19 Serie A home game against Roma (2–1), helping Milan secure the very first competitive victory in the season.