There are many memorable (and tumultuous) seasons in Fiorentina's history, since as a quasi-elitist club its fortunes can range from challenging for the league (though always falling short) to battling relegation survival. Nonetheless, I have enjoyed following and supporting Fiorentina and I believe that the legendary Trappatoni's first season with Fiorentina (1998/1999) was the best in their history, since they led the league for most than half the season and probably would have won the league if Batistuta had not got seriously injured against Milan (eventual champions in a remarkable renaissance) in February 1999. The first choice goalkeeper was consisted of Francesco Toldo 'Toldone' in goal (Italy's number 3/4 goalkeeper at his prime), Pasquale Padalino in defence (often partnered with Tomas Repka or Pierini, both very fine defenders), Sandro Cois in defensive midfield (this guy was a BEAST, especially when partnered with Cristian Amoroso), Rui Costa as attacking midfield (who was not only the best number 10 in history of Fiorentina and Portugal (barring the legendary Giancarlo Antognoni, the man who captained Fiorentina to league glory in the 50s), and, of course, the one and only Gabriel Omar Batistuta, captain, talisman, legend, figurehead and icon in Florence if not beyond (this guy is no doubt one of the best number 9's in football history, since he had everything and could do everything in front of goal). There was also Roberto Baggio, another iconic figure in Italian/world football, and his love for Fiorentina was incredible. Below is the formation in that season:
I have supported Fiorentina since the late 1990s when I was in awe of Gabriel Omar Batistuta, captain and talisman who was not only an inspirational figure on the pitch (believe it or not, he has actually openly stated that he does not like football and finds it boring (!!!)) but the best, most complete and prolific striker in history. Grande Bati!
Manuel Rui Costa
Gabriel Omar Batistuta
My Fiorentina all-time best XI however, differs slightly from this: