Born in Naples, Campania, Montella started his career at Lazio club Aprilia.
In 2005, he was signed by Rieti of Serie C2 — the fourth and lowest division of professional league (until 2014).
[2] Montella joined Lega Pro Seconda Divisione (ex–Serie C2) club F.C.
Montella and teammate Francesco Corapi scored 2 goals in 2010 promotion playoffs, as joint-second-highest scorer in that round, along with Alessandro Cesca (San Marino), Daniel Ciofani (Cisco Roma) and Antonio Gaeta (Legnano).
Montella also scored a brace in 2009–10 Lega Pro Cup, the only goals of the team.
[3] After the match Montella and Corapi replaced Mosciaro and Cardascio as new forward partner of Caputo in 3-4-3 formation, however the club lost 0–1.