Career
Benedettini began his career at San Marino Calcio in Lega Pro, the third tier of the Italian football system. He was first called up to a matchday squad on 24 September 2012, remaining an unused substitute in a 0–1 home loss against Pavia at the Stadio Olimpico in Serravalle. His third call-up on 5 May resulted in his only appearance of the season, in a home match against Cremonese.
Starting goalkeeper Mattia Migani was sent off in the second minute, so forward Francesco Cassola was substituted for Benedettini, who immediately conceded a penalty kick by Giuseppe Le Noci in an eventual 1–6 defeat.
On 21 July 2013, he joined Cesena for an undisclosed fee. He made his senior international debut for San Marino on 27 June 2015, in a Union of European Football Associations Euro 2016 qualifying match against Slovenia in Ljubljana, a 0–6 defeat which was that team"s biggest ever victory.