He began to play in the youth system of AS Roma, he was in the team that finished runners-up in the Torneo di Viareggio 2007.He was among the youngest players in A.S Roma He made his first appearance with the senior squad on 19 December 2007 in the Coppa Italia 2007–08 match lost against Torino F.C., when he substituted Adrian Piţ.
He spent the 2008–09 season on loan to Lega Pro Prima Divisione side Pistoiese.
[3] After his return from Pistoiese, AS Roma decided not to include Della Penna into the first team, thus making him unavailable to play any competitive game at all, since he also cannot be featured any longer with the Primavera side due to age limits, and his contract is due to expire in June 2010.
[5] On 31 August 2010 he moved to Lega Pro Prima Divisione side Ternana in co-ownership deal.
This biographical article related to association football in Italy, about a midfielder born in the 1980s, is a stub.