Jesse Calabro played four seasons for the Humber Hawks men's soccer team spanning from 1997 to 2001. A two time OCAA League All-Star, Jesse ended his career as the second leading scorer all-time with 35 career goals.

1999 was an exceptional year for Calabro as he led the OCAA in scoring and was named his team's MVP. The following year, he was back in the spotlight, once again leading the OCAA in scoring and was recognized as a CCAA All-CAnadian.

In his career, Jesse accumulated two OCAA silver medals, one OCAA gold medal and one CCAA National Championship gold medal. Humber recognized Jesse for his 2000-01 season by naming him Humber's Male Athlete of the Year.

Jesse also played indoor soccer, where his teams earned three OCAA Championship titles.

Calabro was named a member of the OCAA Men's Soccer All-Millennium Team.