Massimo Ferrin attended the University of Alabama at Birmingham for the 2016 and 2017 seasons. In his freshman season he was named to Conference USA All-Conference Freshman team and the following year All-Conference Second-Team. For his Junior and Senior seasons, Massimo transferred to Syracuse University where he scored 12 times. In 2022 Massimo led Vaughan Azzurri to a championship in League 1 Ontario where he scored 23 goals in 15 matches, earning himself League MVP. Massimo joined HFX Wanderers in the CPL for the 2023 season. In his first CPL season, Massimo scored 9 goals and assisted 5.