| Club: | Fiorentina |
| Season: | 1999–2000 |
| Manager: | Giovanni Trapattoni |
| Chairman: | Vittorio Cecchi Gori |
| Chrtitle: | President |
| Stadium: | Artemio Franchi |
| League: | Serie A |
| League Result: | 7th |
| Cup1: | Coppa Italia |
| Cup1 Result: | Quarter-finals |
| Cup2: | UEFA Champions League |
| Cup2 Result: | Second group stage |
| League Topscorer: | Gabriel Batistuta (23) |
| Season Topscorer: | Gabriel Batistuta (29) |
| Leftarm1: | FFFFFF |
| Pattern La1: | _fio00h |
| Body1: | FFFFFF |
| Pattern B1: | _fiore00h |
| Rightarm1: | FFFFFF |
| Pattern Ra1: | _fio00h |
| Pattern Sh1: | _fio00h |
| Shorts1: | FFFFFF |
| Socks1: | 432686 |
| Leftarm2: | FFFFFF |
| Pattern La2: | _fio00a |
| Body2: | FFFFFF |
| Pattern B2: | _fiore00a |
| Rightarm2: | FFFFFF |
| Pattern Ra2: | _fio00a |
| Pattern Sh2: | _fio00a |
| Shorts2: | FFFFFF |
| Socks2: | FFFFFF |
| Leftarm3: | DFDE00 |
| Pattern La3: | _fio00a |
| Body3: | DFDE00 |
| Pattern B3: | _fiore00a |
| Rightarm3: | DFDE00 |
| Pattern Ra3: | _fio00a |
| Pattern Sh3: | _fio00a |
| Shorts3: | DFDE00 |
| Socks3: | DFDE00 |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
Associazione Calcio Fiorentina did not manage to repeat its near-miss season from 1998–99, and instead missed out on qualification to the Champions League, following an inconsistent season. Its topscorer Gabriel Batistuta finally gave up on clinching the Serie A title with Fiorentina, and switched to Roma in the summer, a move which was greeted with controversy since Roma had only finished sixth in the 1999–2000 season.
Fiorentina came close to advancing to the quarter-finals of the Champions League, but ultimately a draw at home against Bordeaux ensured that home wins against Manchester United and Valencia were not enough.
| In | |||||||
|---|---|---|---|---|---|---|---|
| width=3% | Pos. | width=32% | Name | width=30% | from | width=35% | Type |
| FW | |||||||
| MF | |||||||
| FW | |||||||
| FW | |||||||
| DF | Stefano Bettarini | loan ended | |||||
| MF | |||||||
| GK | €2.582 million | ||||||
| DF | |||||||
| DF | |||||||
| MF | |||||||
| FW | Pontedera | ||||||
| MF | Luigi Pagliuca | ||||||
| Out | |||||||
|---|---|---|---|---|---|---|---|
| width=3% | Pos. | width=32% | Name | width=30% | To | width=35% | Type |
| FW | Edmundo | ||||||
| FW | Francesco Flachi | ||||||
| FW | Anselmo Robbiati | ||||||
| MF | Domenico Morfeo | loan | |||||
| DF | Giulio Falcone | ||||||
| FW | Carmine Esposito | ||||||
| DF | Roberto Mirri | ||||||
| DF | Lorenzo Collacchioni | ||||||
| MF | Emiliano Bigica | ||||||
| DF | Stefano Bettarini | ||||||
| Out | |||||||
|---|---|---|---|---|---|---|---|
| width=3% | Pos. | width=32% | Name | width=30% | To | width=35% | Type |
| FW | Luis Airton Oliveira | ||||||
See main article: article and 1999–2000 Serie A.
See main article: article and 1999–2000 Coppa Italia.
See main article: article and 1999–2000 UEFA Champions League.
See main article: article.
See main article: article.
See main article: article.
