| Club: | Milan |
| Season: | 1998–99 |
| Chairman: | Silvio Berlusconi |
| Chrtitle: | President |
| Manager: | Alberto Zaccheroni |
| Stadium: | San Siro |
| League: | Serie A |
| League Result: | Winners (in 1999-2000 UEFA Champions League) |
| Cup1: | Coppa Italia |
| Cup1 Result: | Round of 16 |
| League Topscorer: | Oliver Bierhoff (20) |
| Season Topscorer: | Oliver Bierhoff (20) |
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| Prevseason: | 1997–98 |
| Nextseason: | 1999–2000 |
In the 1998–99 season, Associazione Calcio Milan returned to their previous winning ways under the guidance of new manager Alberto Zaccheroni. Hired from Udinese, Zaccheroni brought striker Oliver Bierhoff and right-wingback Thomas Helveg with him from his former club. He introduced Milan to his unorthodox 3–4–3 formation (in the latter half of the season modified to 3–4–1–2, to allow space for a creative attacking midfielder) in which Bierhoff was a perfect centre forward, scoring 20 goals in the league.
Milan had a marvelous second half of the season, in which they competed for the Serie A title with Lazio and Fiorentina. After seven straight wins in the last seven matches, Milan clinched the scudetto, becoming champions of Italy for the 16th time in their history.[1]
| Squad no. | Name | Nationality | Position | |||
|---|---|---|---|---|---|---|
| Goalkeepers | ||||||
| 12 | Christian Abbiati |  | GK | |||
| 1 | Sebastiano Rossi | | GK | |||
| 31 | Giorgio Frezzolini | | GK | |||
| Defenders | ||||||
| 3 | Paolo Maldini (Captain) | | CB / LB | |||
| 5 | Alessandro Costacurta | | CB / SW / LB / RB | |||
| 14 | Roberto Ayala |  | CB | |||
| 25 | Bruno Ngotty |  | CB | |||
| 17 | Christian Ziege | LB / LM | ||||
| 2 | RB / RM | |||||
| 27 | Francesco Coco | | LB / LM | |||
| 26 | Luigi Sala | | CB | |||
| 19 | Samir Beloufa | CB | ||||
| 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 | |||
| 7 | Ibrahim Ba | | RM / LM | |||
| 21 | Federico Giunti | | CM / AM / DM | |||
| 30 | Domenico Morfeo | | AM / LM / RM | |||
| 8 | Roberto Donadoni | | RM / LM / CM | |||
| Forwards | ||||||
| 20 | Oliver Bierhoff | CF | ||||
| 9 | George Weah |  | CF | |||
| 11 | Maurizio Ganz | | CF | |||
| 16 | Mohammed Aliyu Datti | CF / SS | ||||
| 13 | Alessandro Iannuzzi | | CF | |||
| In | |||||||
|---|---|---|---|---|---|---|---|
| width=3% | Pos. | width=32% | Name | width=30% | from | width=35% | Type |
| FW | Oliver Bierhoff | - | |||||
| MF | Thomas Helveg | - | |||||
| GK | Jens Lehmann | ||||||
| MF | Andres Guly | - | |||||
| DF | Roberto Ayala | - | |||||
| MF | Domenico Morfeo | loan | |||||
| MF | Bruno N'Gotty | ||||||
| DF | Luigi Sala | - | |||||
| GK | Christian Abbiati | ||||||
| FW | Aliyu Datti | ||||||
| MF | Massimo Ambrosini | loan ended | |||||
| DF | Francesco Coco | loan ended | |||||
| FW | Luca Saudati | loan ended | |||||
| Out | |||||||
|---|---|---|---|---|---|---|---|
| width=3% | Pos. | width=32% | Name | width=30% | To | width=35% | Type |
| FW | Patrick Kluivert | ||||||
| FW | Dejan Savicevic | ||||||
| DF | Marcel Desailly | ||||||
| FW | Filippo Maniero | - | |||||
| MF | Giampiero Maini | ||||||
| DF | Steinar Nilsen | ||||||
| DF | Dario Smoje | ||||||
| GK | Gabriele Aldegani | ||||||
| GK | |||||||
| GK | Simone Braglia | ||||||
| DF | Daniele Daino | loan | |||||
| FW | Luca Saudati | loan | |||||
| In | |||||||
|---|---|---|---|---|---|---|---|
| width=3% | Pos. | width=32% | Name | width=30% | from | width=35% | Type |
| GK | Giorgio Frezzolini | loan | |||||
| GK | Dida | ||||||
| MF | Federico Giunti | ||||||
| FW | Alessandro Ianuzzi | loan | |||||
| Out | |||||||
|---|---|---|---|---|---|---|---|
| width=3% | Pos. | width=32% | Name | width=30% | To | width=35% | Type |
| GK | Jens Lehmann | - | |||||
| DF | André Cruz | - | |||||
| DF | Giuseppe Cardone | - | |||||
| GK | Dida | loan | |||||
See main article: 1998–99 Serie A.
See main article: 1998-99 Coppa Italia.
Leonardo 12 George Weah 8 Maurizio Ganz 4 Guly 4