On 21 September 1997, Chimenti made his Serie A debut with the capital club, in a match Roma won 3–1 versus US Lecce.

After displaying decent form with the club, in his three-year spell, Chimenti transferred to Serie A, and European powerhouse, Juventus.

For the 2005–06 Serie A season, Buffon suffered a major injury during pre-season, and was set to miss up to 4 months of action.

After another disappointing season on the Juventus bench, and just 4 additional appearances, the veteran, Chimenti, transferred to Cagliari Calcio on a two-year deal in January 2006.

He originally signed on a season long loan deal in exchange for Emanuele Belardi, who moved in the opposite direction on the same terms.

[4] Chimenti also started the next two games for Juventus against Fulham in the UEFA Europa League, and UC Sampdoria in Serie A, both of which ended in defeats.

[1] Nicknamed Zucchina, Chimenti was known for his physical strength, confidence, longevity, mentality, concentration, and consistency as a goalkeeper, as well as for his ability with the ball at his feet in particular, having played as a forward as a youngster (like his father, Vito), which allowed him to control passes, retain possession under pressure, and even challenge opponents for the ball.

In his youth, his role models were fellow former Juventus goalkeepers Dino Zoff and Stefano Tacconi, who inspired him to change position.

A late bloomer, Chimenti reached his prime in his early 30s, undergoing noticeable improvements under his goalkeeping coach at Lecce, Franco Paleari, who helped him develop his agility, goalkeeping technique, and explosive power, which aided him in his shot-stopping, ability to get to ground quickly, and penalty saving abilities.

[1][5] In October 2022, he joined Serie B club SPAL as a goalkeeping coach following the appointment of Daniele De Rossi as new boss.