| Club: | Roma |
| Season: | 1999–2000 |
| Manager: | Fabio Capello |
| Chairman: | Franco Sensi |
| Chrtitle: | President |
| Stadium: | Stadio Olimpico |
| League: | Serie A |
| League Result: | 6th |
| Cup1: | Coppa Italia |
| Cup1 Result: | Quarter-finals |
| Cup2: | UEFA Cup |
| Cup2 Result: | Fourth round |
| League Topscorer: | Vincenzo Montella (18) |
| Season Topscorer: | Vincenzo Montella (21) |
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| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
The 1999–2000 season saw Associazione Sportiva Roma continue its long drought of titles, finishing a frustrating 6th place in Serie A.
New manager Fabio Capello did not make an immediate impact, and its position actually worsened with one spot, despite 18 goals from Sampdoria signing Vincenzo Montella. Reward for Capello's new 3–4–1–2 system would come in 2000–01, however, when summer signings Gabriel Batistuta, Walter Samuel and Emerson completed the thin squad of the 1999–2000 season, and Roma was able to claim the title. That seemed far away as city rivals Lazio celebrated the 2000 league title.
| No. | Name | Nat | Position(s) | Date of birth (Age) | ||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Goalkeepers | ||||||||||||||||||||||||
| 1 | Francesco Antonioli |  | GK | 1969 9, df=yes (aged) | ||||||||||||||||||||
| 12 | Cristiano Lupatelli | | GK | 1978 6, df=yes (aged) | ||||||||||||||||||||
| 25 | Andrea Campagnolo | | GK | 1978 6, df=yes (aged) | ||||||||||||||||||||
| Defenders | ||||||||||||||||||||||||
| 2 | Cafu |  | RB | 1965 11, df=yes (aged) | ||||||||||||||||||||
| 3 | Zago | | CB | 1969 3, df=yes (aged) | ||||||||||||||||||||
| 6 | Aldair | | CB | 1965 11, df=yes (aged) | ||||||||||||||||||||
| 19 | Sergei Gurenko |  | CB | 1972 9, df=yes (aged) | ||||||||||||||||||||
| 20 | Amedeo Mangone | | CB | 1968 7, df=yes (aged) | ||||||||||||||||||||
| 23 | Alessandro Rinaldi | | CB | 1974 11, df=yes (aged) | ||||||||||||||||||||
| 30 | Fabio Petruzzi | | CB | 1970 10, df=yes (aged) | ||||||||||||||||||||
| 32 | Vincent Candela |  | LB | 1973 10, df=yes (aged) | ||||||||||||||||||||
| Midfielders | ||||||||||||||||||||||||
| 4 | Cristiano Zanetti | | DM | 1977 4, df=yes (aged) | ||||||||||||||||||||
| 5 | Marcos Assunção | | CM | 1976 7, df=yes (aged) | ||||||||||||||||||||
| 8 | Hidetoshi Nakata |  | CM | 1977 1, df=yes (aged) | ||||||||||||||||||||
| 11 | Eusebio Di Francesco | | CM | 1969 9, df=yes (aged) | ||||||||||||||||||||
| 13 | Manuele Blasi | | LM | 1980 8, df=yes (aged) | ||||||||||||||||||||
| 17 | Damiano Tommasi | | DM | 1974 5, df=yes (aged) | ||||||||||||||||||||
| 16 | Ivan Tomić | CM | 1976 1, df=yes (aged) | |||||||||||||||||||||
| Strikers | ||||||||||||||||||||||||
| 7 | Gustavo Bartelt |  | CF | 1974 9, df=yes (aged) | ||||||||||||||||||||
| 9 | Vincenzo Montella | | CF | 1974 6, df=yes (aged) | ||||||||||||||||||||
| 10 | Francesco Totti (c) | | FW | 1976 9, df=yes (aged) | ||||||||||||||||||||
| 18 | Paolo Poggi | | CF | 1971 2, df=yes (aged) | ||||||||||||||||||||
| 24 | Marco Delvecchio | | CF | 1973 4, df=yes (aged) | ||||||||||||||||||||
| 27 | Fábio Júnior | | CF | 1977 11, df=yes (aged) | ||||||||||||||||||||
| In | |||||||
|---|---|---|---|---|---|---|---|
| width=3% | Pos. | width=32% | Name | width=30% | from | width=35% | Type |
| FW | Vincenzo Montella | €25.82 million | |||||
| MF | Hidetoshi Nakata | €21.69 million | |||||
| GK | Francesco Antonioli | ||||||
| MF | Marcos Assunção | ||||||
| MF | Cristiano Zanetti | ||||||
| FW | Paolo Poggi | ||||||
| GK | Cristiano Lupatelli | ||||||
| DF | Sergei Gurenko | ||||||
| DF | Amedeo Mangone | ||||||
| DF | Joseph Dayo Oshadogan | ||||||
| DF | Filippo Dal Moro | ||||||
| MF | Neşat Gülünoğlu | ||||||
| MF | Giuseppe Colucci | ||||||
| MF | Manuele Blasi | ||||||
| Out | |||||||
|---|---|---|---|---|---|---|---|
| width=3% | Pos. | width=32% | Name | width=30% | To | width=35% | Type |
| FW | Paulo Sérgio | €6.60 million | |||||
| GK | Michael Konsel | free | |||||
| MF | Luigi Di Biagio | ||||||
| DF | Pierre Womé | ||||||
| GK | Antonio Chimenti | ||||||
| GK | Giorgio Sterchele | ||||||
| DF | Omari Tetradze | ||||||
| DF | Luca Ferri | ||||||
| DF | Filippo Dal Moro | loan | |||||
| DF | Marco Quadrini | ||||||
| DF | Joseph Dayo Oshadogan | ||||||
| MF | Daniele Conti | ||||||
| MF | Neşat Gülünoğlu | free | |||||
| MF | Dmitri Alenichev | loan | |||||
| MF | Giuseppe Colucci | loan | |||||
| MF | Daniele De Vezze | ||||||
| MF | Alessandro Frau | ||||||
| FW | Lampros Choutos | ||||||
| FW | Carmine Gautieri | ||||||
| style=text-align:center; width:150px; | Competition | style=text-align:center; width:100px; | Started round | style=text-align:center; width:100px; | Final position | style=text-align:center; width:150px; | First match | style=text-align:center; width:140px; | Last match |
|---|---|---|---|---|---|---|---|---|---|
| style=text-align:left; | Serie A | Matchday 1 | 6th | 29 August 1999 | 14 May 2000 | ||||
| style=text-align:left; | Coppa Italia | Round of 16 | Quarter-finals | 1 December 1999 | 25 January 2000 | ||||
| style=text-align:left; | UEFA Cup | First round | Fourth round | 16 September 1999 | 9 March 2000 |
See main article: 1999–2000 Serie A.
See main article: 1999–2000 Coppa Italia.
See main article: 1999–2000 UEFA Cup.
See main article: 1999–2000 UEFA Cup first round.
See main article: 1999–2000 UEFA Cup second round.
See main article: 1999–2000 UEFA Cup third round.
Vincenzo Montella 18 (4) Marco Delvecchio 11 Francesco Totti 7 (4) Vincent Candela 3