Fiore was born in Cosenza, and he began his professional footballing career with his domestic club in 1992. He played just 11 games before moving to Parma in 1994. He made his Serie A debut with the club at the age of nineteen, in a 0–0 away draw against Genoa, on 11 December 1994. During that season, Parma came in third in Serie A, and reached the final of the Coppa Italia. Their most prestigious success was achieved with their UEFA Cup victory over season rivals Juventus, and Fiore was inserted into the starting eleven by manager Nevio Scala, in the return leg of the final, which finished 1–1. This allowed Fiore to gain international experience alongside his established teammates such as Gianfranco Zola, Fernando Couto, and Dino Baggio. His limited playing time with them persuaded him to move to Padova for the following season, where he scored 1 goal in 24 games. In the 1996–97 season, Fiore moved to Serie B side Chievo, where he was impressive, notching up 2 goals and plenty of assists. This prompted former club, Parma, to re-sign the midfielder in 1997. For the next 2 seasons he became a more permanent member of the squad; although he was mainly left on the bench during the 1997–98 season, he looked far more impressive than his main starting eleven contender, the ageing Dino Baggio, when he was given a chance, and he became a member of the starting line-up during the following 1998–99 season. This season was Fiore's most successful season, as Parma finished fourth in Serie A, and won the Coppa Italia over Fiorentina. Fiore also won his second career UEFA Cup with Parma that season, as they defeated Olympique Marseille 3–0 in the final in Moscow. Fiore was one of the protagonists of Parma's triumphant European campaign that season, notching 2 goals in 10 UEFA Cup appearances.