Calabro's playing career started as a youth player for Lazio, with whom he only appeared once as an unused substitute in a Rome derby against Roma on 24 October 1993.
[4][7] As Virtus Francavilla coach, Calabro succeeded in winning two consecutive promotions, leading the small club from Salento from the amateur leagues to the professional ranks of Lega Pro, and then to a place in the promotion playoffs of the 2016–17 Lega Pro after ending the season with an impressive fifth place in the final table.
[10] On 21 January 2019, he was named new head coach of Serie C outfit Viterbese, replacing Stefano Sottili.
[15] On 29 November 2021, he was fired by Catanzaro with his staff: Alberto Villa, Pasquale Visconti, Alessandro Imbrogno,[16] Antonio Raione.
[17] On 26 May 2022, Virtus Francavilla announced to have re-hired Calabro as their new head coach on a two-year deal, effective from 1 July 2022.