Province of Pesaro and Urbino
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 D seasons.