On 9 August 2024, Di Maggio joined Serie C club Perugia on a season-long loan.
[1] Two days later, Di Maggio made his professional debut, coming on as a substitute in the Coppa Italia Serie C fixture against Latina.
In May 2022, Di Maggio took part in the 2022 UEFA European Under-17 Championship, in which Italy got eliminated in the quarter-finals, making four appearances and scoring one goal.
[3] In July 2024, Di Maggio participated in the 2024 UEFA European Under-19 Championship, making four appearances and scoring one goal.
[4] Described as a modern mezzala, Di Maggio is praised for his workrate, determination, attacking runs and shooting abilities.