In the 1998-1999 season, Associazione Calcio Fiorentina had a strong start in Serie A but ultimately finished third in the league, securing qualification for the UEFA Champions League in the following season. Their European journey in that season was cut short due to an incident where a handmade bomb was thrown at a linesman during a match against Grasshoppers. Despite winning the match, Fiorentina was declared losers and removed from the tournament. Additionally, Fiorentina lost the Coppa Italia Final to Parma, resulting in a season without any major titles.
Key players during this season included Gabriel Batistuta, Rui Costa, and Francesco Toldo, who stood out. Defensive issues and goals conceded were cited as the main reasons Fiorentina fell short in their title bid in Serie A.