Тернана
Silvestri began his professional career at the age of 20, after he was promoted from the youth system of Ternana Calcio in 1995. The player made a handful of appearances in his first season, and continued with the senior squad for 4 full seasons, and in his final two seasons with the club, Silvestri established himself as an undisputed starter an following the conclusion of the 1998–99 season, Silvestri had racked up over 100 appearances for his club in all competitions, scoring 6 goals. Following several positive seasons with Ternana Calcio, the fullback transferred to Cosenza Calcio in the summer of 1999.