# 1999–2000 AC Milan season

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.

## Players
### Squad information

| Squad no. | Name | 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 | Thomas Helveg | 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 |

### Left club during the season

Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply. Players may hold more than one non-FIFA nationality.
| No. | Pos. | Nation | Player |
| 9 | FW | LBR | George Weah |
| 11 | FW | ITA | Maurizio Ganz |
| 25 | DF | FRA | Bruno Ngotty |
| 28 | GK | ITA | Roberto Colombo |

### Transfers

In :
| Pos. | Name | from | Type |
| FW | Andriy Shevchenko | Dinamo Kyiv | - |
| MF | Gennaro Gattuso | U.S. Salernitana | - |
| MF | Serginho | Sao Paulo FC | - |
| GK | Valerio Fiori | Piacenza Calcio | - |
| DF | Mirco Sadotti | U.S. Lecce | - |
| DF | Max Tonetto | Empoli F.C. | - |
| DF | Carlo Teodorani | Cesena F.C. | - |
| MF | Diego De Ascentis | A.S. Bari | - |
| MF | Pierluigi Orlandini | Parma F.C. | - |
| FW | Mattia Graffiedi | Cesena FC | - |
| GK | Dida | FC Lugano | loan ended |
| DF | André Cruz | Standard Liege | loan ended |
| DF | Daniele Daino | S.S.C. Napoli | loan ended |
| GK | Gabriele Aldegani | A.C. Monza | loan ended |
| FW | Luca Saudati | Como 1907 | loan ended |
Out :
| Pos. | Name | To | Type |
| MF | Roberto Donadoni | | retired |
| DF | André Cruz | Torino F.C. | |
| GK | Massimo Taibi | Venezia F.C. | |
| MF | Christian Ziege | Middlesbrough F.C. | |
| MF | Ibrahim Ba | Perugia Calcio | |
| DF | Samir Beloufa | A.C. Monza | loan |
| DF | Francesco Coco | Torino F.C. | loan |
| GK | Gabriele Aldegani | Treviso FBC 1993 | loan |
| GK | Dida | SC Corinthians | loan |
| GK | Giorgio Frezzolini | Inter | co-ownership |
| DF | Daniele Daino | Perugia Calcio | loan |
| DF | Steinar Nilsen | S.S.C. Napoli | co-ownership |
| DF | Carlo Teodorani | Ternana Calcio | loan |
| MF | Domenico Morfeo | Fiorentina | loan ended |
| FW | Alessandro Ianuzzi | Reggina | loan |
| FW | Luca Saudati | Empoli F.C. | loan |

#### Winter

In :
| Pos. | Name | from | Type |
| DF | José Chamot | Atletico Madrid | - |
| DF | Fabricio Coloccini | Boca Juniors | - |
| DF | Taribo West | Inter | - |
| FW | José Mari | Atletico Madrid | - |
Out :
| Pos. | Name | To | Type |
| GK | Roberto Colombo | Calcio Padova | loan |
| DF | Bruno N'Gotty | Venezia F.C. | loan |
| DF | Mirco Sadotti | U.S. Lecce | loan |
| DF | Max Tonetto | Bologna F.C. | loan |
| MF | Pierluigi Orlandini | Venezia F.C. | loan |
| FW | Maurizio Ganz | Venezia F.C. | loan |
| FW | George Weah | Chelsea F.C. | loan |

### Reserves

Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply. Players may hold more than one non-FIFA nationality.
| No. | Pos. | Nation | Player |
| 30 | FW | ITA | Mattia Graffiedi |
| 31 | MF | ITA | Lorenzo Rossetti |
| 32 | FW | ITA | Andrea Rabito |
| 35 | MF | ITA | Simonluca Agazzone |
| 36 | DF | ITA | Michele Ferri |

### Kits

| Home | Away | Third | Third Alt. | Centennial |

## Competitions
### Serie A
#### League table

| Pos | Teamvte | Pld | W | D | L | GF | GA | GD | Pts | Qualification or relegation |
| 1 | Lazio (C) | 34 | 21 | 9 | 4 | 64 | 33 | +31 | 72 | Qualification to Champions League first group stage |
| 2 | Juventus | 34 | 21 | 8 | 5 | 46 | 20 | +26 | 71 | Qualification to Champions League first group stage |
| 3 | Milan | 34 | 16 | 13 | 5 | 65 | 40 | +25 | 61 | Qualification to Champions League third qualifying round |
| 4 | Internazionale | 34 | 17 | 7 | 10 | 58 | 36 | +22 | 58 | Qualification to Champions League third qualifying round |
| 5 | Parma | 34 | 16 | 10 | 8 | 52 | 37 | +15 | 58 | Qualification to UEFA Cup first round |
* ↑ Internazionale entered the 2000–01 UEFA Champions League after winning the UEFA Champions League qualification match against Parma.

#### Results summary

| Overall | Overall | Overall | Overall | Overall | Overall | Overall | Overall | Home | Home | Home | Home | Home | Home | Away | Away | Away | Away | Away | Away |
Source: Competitive matches

#### Results by round

| Round | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 | 32 | 33 | 34 |
| Ground | A | H | A | H | A | H | A | A | H | A | H | A | H | H | A | H | A | H | A | H | A | H | A | H | H | A | H | A | H | A | A | H | A | H |
| Result | D | W | D | W | D | D | W | D | W | L | W | L | W | D | W | D | W | D | W | W | W | W | D | L | D | L | W | L | D | D | W | W | D | W |
| Position | 4 | 1 | 5 | 3 | 5 | 5 | 3 | 3 | 3 | 5 | 4 | 6 | 5 | 5 | 5 | 5 | 5 | 4 | 3 | 3 | 3 | 2 | 3 | 4 | 4 | 4 | 3 | 3 | 3 | 4 | 3 | 3 | 3 | 3 |

#### Matches
### UEFA Champions League
#### Group stage

| Pos | Teamvte | Pld | W | D | L | GF | GA | GD | Pts | Qualification | CHE | HER | GAL | MIL |
| 1 | Chelsea | 6 | 3 | 2 | 1 | 10 | 3 | +7 | 11 | Advance to second group stage | — | 2–0 | 1–0 | 0–0 |
| 2 | Hertha BSC | 6 | 2 | 2 | 2 | 7 | 10 | −3 | 8 | Advance to second group stage | 2–1 | — | 1–4 | 1–0 |
| 3 | Galatasaray | 6 | 2 | 1 | 3 | 10 | 13 | −3 | 7 | Transfer to UEFA Cup | 0–5 | 2–2 | — | 3–2 |
| 4 | Milan | 6 | 1 | 3 | 2 | 6 | 7 | −1 | 6 | | 1–1 | 1–1 | 2–1 | — |

## Statistics
### Players statistics

| No. | Pos | Nat | Player | Total | Total | Serie A | Serie A | Coppa Italia | Coppa Italia | UEFA Champions League | UEFA Champions League |
| No. | Pos | Nat | Player | Apps | Goals | Apps | Goals | Apps | Goals | Apps | Goals |
| 12 | GK | ITA | Abbiati | 35 | -40 | 29 | -33 | 0 | 0 | 6 | -7 |
| 5 | DF | ITA | Costacurta | 34 | 0 | 27 | 0 | 2 | 0 | 5 | 0 |
| 26 | DF | ITA | Sala | 24 | 0 | 16+4 | 0 | 3 | 0 | 1 | 0 |
| 3 | DF | ITA | Maldini | 37 | 1 | 27 | 1 | 4 | 0 | 6 | 0 |
| 24 | MF | ARG | Guly | 32 | 3 | 19+4 | 1 | 4 | 2 | 5 | 0 |
| 23 | MF | ITA | Ambrosini | 35 | 2 | 25+4 | 2 | 4 | 0 | 2 | 0 |
| 4 | MF | ITA | Albertini | 32 | 1 | 23+3 | 1 | 1 | 0 | 5 | 0 |
| 8 | MF | ITA | Gattuso | 28 | 1 | 16+6 | 1 | 1 | 0 | 5 | 0 |
| 27 | MF | BRA | Serginho | 31 | 2 | 18+6 | 2 | 2 | 0 | 5 | 0 |
| 20 | FW | GER | Bierhoff | 39 | 14 | 28+2 | 11 | 3 | 1 | 6 | 2 |
| 7 | FW | UKR | Shevchenko | 42 | 29 | 30+2 | 24 | 4 | 4 | 6 | 1 |
| 1 | GK | ITA | Rossi | 9 | -14 | 5 | -7 | 4 | -7 |
| 14 | DF | ARG | Ayala | 22 | 0 | 9+4 | 0 | 3 | 0 | 6 | 0 |
| 13 | DF | NGA | Taribo West | 4 | 1 | 3+1 | 1 |
| 2 | MF | DEN | Helveg | 32 | 0 | 10+17 | 0 | 1 | 0 | 4 | 0 |
| 19 | DF | ARG | Chamot | 14 | 0 | 13 | 0 | 1 | 0 |
| 38 | DF | ARG | Coloccini | 0 | 0 | 0 | 0 |
| 18 | MF | BRA | Leonardo | 26 | 6 | 11+9 | 4 | 1 | 1 | 5 | 1 |
| 10 | MF | CRO | Boban | 22 | 6 | 11+6 | 6 | 3 | 0 | 2 | 0 |
| 21 | MF | ITA | Giunti | 32 | 1 | 11+13 | 0 | 3 | 0 | 5 | 1 |
| 15 | MF | ITA | De Ascentis | 23 | 0 | 14+5 | 0 | 4 | 0 |
| 41 | FW | ESP | José Mari | 17 | 1 | 6+9 | 1 | 2 | 0 |
| 33 | FW | NGA | Aliyu Datti | 1 | 0 | 0+1 | 0 |
| 9 | FW | LBR | Weah | 13 | 5 | 8+2 | 4 | 2 | 0 | 1 | 1 |
| | MF | FRA | N'Gotty | 12 | 0 | 7+2 | 0 | 1 | 0 | 2 | 0 |
| | MF | ITA | Orlandini | 5 | 1 | 1+1 | 1 | 1 | 0 | 2 | 0 |
| | FW | ITA | Ganz | 3 | 1 | 0+1 | 1 | 1 | 0 | 1 | 0 |
| 40 | GK | ITA | Fiori | 0 | 0 | 0 | 0 |
| | DF | ITA | Tonetto | 1 | 0 | 0 | 0 | 1 | 0 |
* Source: http://calcio-seriea.net/presenze/1999/1171/

### Goalscorers

* Andriy Shevchenko 24
* Oliver Bierhoff 11
* Zvonimir Boban 5
* Leonardo 4
* George Weah 3