Career
Born in Fano, the second largest town (by population) in the Province of Pesaro and Urbino, Gentili started his career with Vis Pesaro. After a season with Perugia, he was loaned to Internazionale He played once for Inter first team in a friendly match. However, Inter did not buy him and Gentili returned to Fano and played 2 Serie Doctorate seasons.
In August 2007, he signed a 1-year contract with, but now as a right back.
He only managed to play for Ancona at 2007-2008 Coppa Italia Serie C.
In January 2008, he was signed by Valle del Giovenco. After the club promoted to Lega Pro Prima Divisione, he was released.
In 2009-2010 season, he played for Serie Doctorate side Real Montecchio and in next season left for Fossombrone after Montecchio relegated. Both clubs were located inside the Province of Pesaro and Urbino.
