| Club: | Milan |
| Season: | 1999–2000 |
| Manager: | Alberto Zaccheroni |
| Chairman: | Silvio Berlusconi |
| Chrtitle: | President |
| Stadium: | San Siro |
| League: | Serie A |
| League Result: | 3rd |
| Cup1: | Supercoppa Italiana |
| Cup1 Result: | Runners-up |
| Cup2: | Coppa Italia |
| Cup2 Result: | Quarter-finals |
| Cup3: | UEFA Champions League |
| Cup3 Result: | Group stage |
| League Topscorer: | Andriy Shevchenko (24) |
| Season Topscorer: | Andriy Shevchenko (29) |
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| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
Associazione Calcio Milan did not manage to repeat their successful previous season (1998–99). They failed to defend the Serie A title, finishing in 3rd place behind champions Lazio and runners-up Juventus, and crashed out of the Champions League following a lackluster performance in the First Group Phase. In fact, Milan ended up last in the group, and did not even qualify for the remainder of the UEFA Cup.
New signing Andriy Shevchenko played his first season with the Milanese club, and managed to become the Serie A's top scorer in his debut season in Italy, with 24 goals (29 in all competitions), further enhancing his reputation as a fearsome striker. Other signings proven to be successful were Serginho and Gennaro Gattuso, who would stay at the club for years to come and be eventually introduced into the club's hall of fame.
| Squad no. | Name | Nationality | Position | |||
|---|---|---|---|---|---|---|
| Goalkeepers | ||||||
| 12 | Christian Abbiati |  | GK | |||
| 1 | Sebastiano Rossi | | GK | |||
| 40 | Valerio Fiori | | GK | |||
| Defenders | ||||||
| 3 | Paolo Maldini (Captain) | | CB / LB | |||
| 5 | Alessandro Costacurta | | CB / SW / LB / RB | |||
| 14 | Roberto Ayala |  | CB | |||
| 13 | Taribo West | LB / CB | ||||
| 2 | RB / RM | |||||
| 19 | José Chamot | | LB / RB / CB | |||
| 26 | Luigi Sala | | CB | |||
| 38 | Fabricio Coloccini | | CB | |||
| 27 | Serginho |  | LB / LM / LW | |||
| Midfielders | ||||||
| 4 | Demetrio Albertini | | CM / DM | |||
| 18 | Leonardo | | AM / LW | |||
| 10 | Zvonimir Boban | AM / CM / LW / RW | ||||
| 24 | Guly | | LM / RM / AM | |||
| 23 | Massimo Ambrosini | | CM / DM | |||
| 8 | Gennaro Gattuso | | CM / DM / RM | |||
| 21 | Federico Giunti | | CM / AM / DM | |||
| 15 | Diego De Ascentis | | CM / DM | |||
| 34 | Carlo Teodorani | | LM / LB | |||
| Forwards | ||||||
| 20 | Oliver Bierhoff | CF | ||||
| 7 | Andriy Shevchenko |  | CF | |||
| 41 | José Mari |  | CF / SS | |||
| 33 | Mohammed Aliyu Datti | CF / SS | ||||
| In | |||||||
|---|---|---|---|---|---|---|---|
| width=3% | Pos. | width=32% | Name | width=30% | from | width=35% | Type |
| FW | Andriy Shevchenko | - | |||||
| MF | Gennaro Gattuso | - | |||||
| MF | Serginho | - | |||||
| GK | Valerio Fiori | - | |||||
| DF | Mirco Sadotti | - | |||||
| DF | Max Tonetto | - | |||||
| DF | Carlo Teodorani | - | |||||
| MF | Diego De Ascentis | - | |||||
| MF | Pierluigi Orlandini | - | |||||
| FW | Mattia Graffiedi | - | |||||
| GK | Dida | loan ended | |||||
| DF | André Cruz | loan ended | |||||
| DF | Daniele Daino | loan ended | |||||
| GK | Gabriele Aldegani | loan ended | |||||
| FW | Luca Saudati | loan ended | |||||
| Out | |||||||
|---|---|---|---|---|---|---|---|
| width=3% | Pos. | width=32% | Name | width=30% | To | width=35% | Type |
| MF | Roberto Donadoni | retired | |||||
| DF | André Cruz | ||||||
| GK | |||||||
| MF | Christian Ziege | ||||||
| MF | Ibrahim Ba | ||||||
| DF | Samir Beloufa | loan | |||||
| DF | Francesco Coco | loan | |||||
| GK | Gabriele Aldegani | loan | |||||
| GK | Dida | loan | |||||
| GK | Giorgio Frezzolini | co-ownership | |||||
| DF | Daniele Daino | loan | |||||
| DF | Steinar Nilsen | co-ownership | |||||
| DF | Carlo Teodorani | loan | |||||
| MF | Domenico Morfeo | loan ended | |||||
| FW | Alessandro Ianuzzi | loan | |||||
| FW | Luca Saudati | loan | |||||
| In | |||||||
|---|---|---|---|---|---|---|---|
| width=3% | Pos. | width=32% | Name | width=30% | from | width=35% | Type |
| DF | José Chamot | - | |||||
| DF | Fabricio Coloccini | - | |||||
| DF | Taribo West | - | |||||
| FW | José Mari | - | |||||
| Out | |||||||
|---|---|---|---|---|---|---|---|
| width=3% | Pos. | width=32% | Name | width=30% | To | width=35% | Type |
| GK | Roberto Colombo | loan | |||||
| DF | Bruno N'Gotty | loan | |||||
| DF | loan | ||||||
| DF | Max Tonetto | loan | |||||
| MF | Pierluigi Orlandini | loan | |||||
| FW | Maurizio Ganz | loan | |||||
| FW | George Weah | loan | |||||
See main article: 1999 Supercoppa Italiana.
See main article: 1999–2000 Serie A.
See main article: 1999–2000 Coppa Italia.
See main article: 1999–2000 UEFA Champions League.
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