[2] Fiore played for several Italian clubs throughout his career; he started out with Cosenza in 1992, before moving to Parma for a season in 1994, where he made his Serie A debut and won the UEFA Cup.

He subsequently moved to Udinese, where he spent two successful seasons, winning the UEFA Intertoto Cup in 2000 and thus helping his team qualify for Europe.

His performances led to a transfer to Spanish side Valencia later that year, where he struggled to replicate his previous form despite initially winning the UEFA Supercup, and he was subsequently sent back to Italy on loan to Fiorentina, Torino, and Livorno during his three seasons with the club.

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.

Fiore could not find his best form for Lazio during the 2001–02 season, as the coach that replaced Zoff, Alberto Zaccheroni, persisted in playing him on the left side of midfield.

Due to the financial problems which Lazio were suffering, Fiore, along with Bernardo Corradi, were off-loaded to Spanish club Valencia, where he joined the Italian coach Claudio Ranieri, and compatriot Marco Di Vaio, signing a 3+1 years contract.

After a promising start, which included winning the UEFA Super Cup over Champions League winners Porto, Valencia suffered a disastrous losing streak in October, from which they never fully recovered.

Fiore linked up well with striker Luca Toni, and together they brought Fiorentina to a higher level, guiding them to 4th in Serie A, before the Calciopoli verdicts saw them lose this place.

Fiorentina decided not to take Fiore on a permanent basis and he sealed a loan move to Torino, who were returning to Serie A, on deadline day.

Successively, Fiore did not play for any team during the 2008–09, but in September 2009 he finally made his comeback into active football, agreeing a three-year contract with hometown club Cosenza, in the third-tier Lega Pro Prima Divisione, where he remained until his retirement in 2011.

He made his debut for the senior national team during his time with Udinese, under manager Dino Zoff, on 23 February 2000, taking part in a 1–0 victory in an international friendly against Sweden, in Palermo.

[16][17] His fine form continued as he went on to take part in all of Italy's matches throughout the competition, as they reached the final, only to lose to the defending World Champions France on a golden-goal in extra-time.

[18] Under Zoff's replacement Giovanni Trapattoni, Fiore continued to be a member of the national side, scoring his second international goal on 28 February 2001, in a friendly defeat to Argentina, at the Stadio Olimpico in Rome.