In 1999, he transferred to US Lecce on a three-year deal. He was instantly inserted into the club's starting line-up and made 33 appearances for his new club, in his first season. He appeared an additional 34 times during 2000–01 Serie A campaign, and totaled 31 appearances the following season. After displaying decent form with the club, in his three-year spell, Chimenti transferred to Serie A, and European powerhouse, Juentus.