Di Benedetto started his career at Abruzzese club Pescara.
Juventus
On 17 August 2011 Di Benedetto was signed by Juventus for €450,000,[2] rejoining former Pescara team-mate Luca Del Papa. Di Benedetto only played 8 times for the reserve team in the 2012–13 season.[3] Di Benedetto signed his first professional contract in 2013, keeping him until 2016.[4] Di Benedetto played twice in 2013–14 UEFA Youth League.[5]
On 8 July 2015 Serie B club Lanciano signed Di Benedetto and Penna from Juventus,[8] as part of the deal that Mame Baba Thiam moved to Turin outright in June.
Later career
After four months at L'Aquila, Di Benedetto joined Polisportiva Torrese 1974 in December 2019.[9] On 12 August 2020, he moved to Nereto Calcio.[10] On 8 April 2021, Di Benedetto signed with Lanciano.[11] In July 2021, he joined ASD Sambuceto Calcio.[12]