Born in Assisi, the Province of Perugia, Umbria region, Benedetti started his career at Milan as a trainee: he was the member of the under-17 team in 2006–07 as well as the reserve B mainly for under-18 players in 2007–08 season. Benedetti left for Umbrian club Orvietana for 2009–10 Serie D. In the next season he was signed by re-established Perugia for 2010–11 Serie D. Benedetti won the champion of Group E as well as the grand runner-up of the fifth division, losing to Cuneo of Group A. Benedetti made 32 out of possible 42 appearances in 2011–12 Lega Pro Seconda Divisione. Benedetti missed 3 games due to suspensions, as he was booked 11 times. He also won 2012 Supercoppa di Lega di Seconda Divisione. Despite included in the pre-season camp of Perugia, On 31 August 2012 Benedetti was signed by Catanzaro.
