Chiesa played for several Italian clubs throughout his career, and performed regularly in Serie A for over a decade, winning titles with Sampdoria, Parma, and Fiorentina; he later also spent a spell with Lazio.
During his time at the club, he also formed a successful partnership with Argentine star striker Hernán Crespo, as the duo averaged 10–15 goals a season each.
[7][8] In 1999, he was signed by Fiorentina for 28 billion lire (€14.46 million),[10] a team looking to expand and bring in better players, in an attempt to keep club captain and talisman Gabriel Batistuta.
Despite making regular appearances in his first season for La Viola, Chiesa was fighting for a place with Predrag Mijatović among others, and also had spells where he was out of form, and in the end only managed 6 goals in the League.
Meanwhile, Chiesa became the main striker for the club under manager Roberto Mancini, supported by playmaker Rui Costa,[8] and scored 22 goals in 30 matches, finishing amongst the top 5 highest scorers in the league and helping Fiorentina to win the 2000–01 Coppa Italia over his former club, Parma, in the final; in the second leg at home, he set up Nuno Gomes's goal in a 1–1 draw, which allowed Fiorentina to clinch the title 2–1 on aggregate.
[17] He was subsequently selected by manager Arrigo Sacchi to play for Italy at the UEFA Euro 1996 tournament later that year, ahead of other established strikers such as Roberto Baggio, Gianluca Vialli, and Giuseppe Signori.
[25] Under manager Dino Zoff, Chiesa appeared in Italy's 6–2 friendly win over the FIFA World Stars on 16 December 1998, organised to commemorate the centenary of the Italian Football Federation, scoring a hat-trick.
[28] Alongside Alessandro Del Piero, Chiesa holds the unique record for the most goals scored by an Italian international coming off the bench (5).
Possessing pace, stamina, good offensive movement, and a powerful and accurate shot with either foot from both inside and outside the box, he excelled during counter-attacks, and was known for his ability to make attacking runs into the area, and quickly strike the ball first time while on the run; he was also equally known for his ability to score with powerful or bending strikes from free-kicks, and is the joint ninth-highest goalscorer of all time from free kicks in Serie A, with 13 goals, alongside Michel Platini and Álvaro Recoba.