| 1999–2000 season | |||
| Manager | Alberto Zaccheroni | ||
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| Serie A | 3rd | ||
| Coppa Italia | Quarter-finals | ||
| Champions League | First group stage | ||
| Supercoppa Italiana | Runners-up | ||
| Top goalscorer | League: Andriy Shevchenko (24) All: Andriy Shevchenko (29) |
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A.C. Milan did not repeat its successful season in 1998–99, and fell back to third in Serie A, as well as crashing out of the Champions League, following a lackluster performance in the First Group Phase. In fact, Milan ended up last in the group, and was not even qualifying for the remainder of the UEFA Cup.
Andriy Shevchenko played his first season with the Milanese club, and managed to become top scorer already in his debut season. The Ukrainian further enhanced his reputation as a fearsome striker, which was good riddance for Milan, considering Oliver Bierhoff's scoring tally's decline. The team showed signs of being over the hill, having had several aging players while it won the league in 1998–99.
Contents |
| 1 | Lecce | 2–2 | Milan | |||
| Savino 65' Lucarelli 80' |
Weah 55' Shevchenko 73' |
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| 2 | Milan | 3–1 | Perugia | |||
| Bierhoff 28' Shevchenko 59' Leonardo 71' |
Materazzi 40' | |||||
| 3 | Bari | 1–1 | Milan | |||
| Osmanovski 12' | Serginho 34' | |||||
| 4 | Milan | 4–0 | Bologna | |||
| Weah 9' Leonardo 44' Bierhoff 55' (pen.) Ganz 63' |
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| 5 | Lazio | 4–4 | Milan | |||
| Verón 18' Simeone 36' Salas 38', 72' |
Mihajlović 35' (o.g.) Shevchenko 43', 63' (pen.), 69' |
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| 6 | Milan | 2–2 | Cagliari | |||
| Shevchenko 11' (pen.) Bierhoff 83' |
Morfeo 8' Berretta 39' |
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| 7 | Internazionale | 1–2 | Milan | |||
| Ronaldo 20' (pen.) | Shevchenko 28' Weah 89' |
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| 8 | Verona | 0–0 | Milan | |||
| 9 | Milan | 3–0 | Venezia | |||
| Bierhoff 52' Weah 63' Orlandini 74' |
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| 10 | Juventus | 3–1 | Milan | |||
| Conte 23' Inzaghi 51' Kovačević 90' |
Zidane 21' (o.g.) | |||||
| 11 | Milan | 2–1 | Parma | |||
| Boban 8' Maldini 50' |
Crespo 46' | |||||
| 12 | Fiorentina | 2–1 | Milan | |||
| Batistuta 22' Heinrich 42' |
Bierhoff 1' | |||||
| 13 | Milan | 2–0 | Torino | |||
| Bierhoff 3' Shevchenko 76' (pen.) |
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| 14 | Milan | 2–2 | Reggina | |||
| Shevchenko 61', 74' | Pirlo 30' Kallon 79' |
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| 15 | Piacenza | 0–1 | Milan | |||
| Bierhoff 31' | ||||||
| 16 | Milan | 2–2 | Roma | |||
| Bierhoff 38' José Mari 68' |
Delvecchio 8' Montella 57' |
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| 17 | Udinese | 1–2 | Milan | |||
| Muzzi 86' | Boban 40' Shevchenko 61' |
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| 18 | Milan | 2–2 | Lecce | |||
| Maldini 62' Bierhoff 69' |
Lucarelli 29', 56' | |||||
| 19 | Perugia | 0–3 | Milan | |||
| Shevchenko 69', 73', 76' | ||||||
| 20 | Milan | 4–1 | Bari | |||
| Boban 15' Serginho 52' Innocenti 84' (o.g.) Shevchenko 88' |
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| 21 | Bologna | 2–3 | Milan | |||
| Ingesson 58' Eriberto 59' |
Gattuso 32' Shevchenko 48' Bierhoff 57' |
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| 22 | Milan | 2–1 | Lazio | |||
| Boban 38' (pen.), 45' (pen.) | S. Inzaghi 82' | |||||
| 23 | Cagliari | 0–0 | Milan | |||
| 24 | Milan | 1–2 | Internazionale | |||
| Shevchenko 90' (pen.) | Zamorano 43' Di Biagio 63' |
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| 25 | Milan | 3–3 | Verona | |||
| Albertini 16' Shevchenko 33', 59' (pen.) |
Apolloni 51' Laursen 54' Cammarata 90+3' |
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| 26 | Venezia | 1–0 | Milan | |||
| Maniero 11' | ||||||
| 27 | Milan | 2–0 | Juventus | |||
| Shevchenko 45', 84' (pen.) | ||||||
| 28 | Parma | 1–0 | Milan | |||
| Crespo 68' | ||||||
| 29 | Milan | 1–1 | Fiorentina | |||
| Leonardo 76' | Di Livio 70' | |||||
| 30 | Torino | 2–2 | Milan | |||
| Pinga 29', 69' | Ambrosini 13' Guly 74' |
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| 31 | Reggina | 1–2 | Milan | |||
| Pirlo 25' | Vargas 5' (o.g.) Shevchenko 14' |
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| 32 | Milan | 1–0 | Piacenza | |||
| Ambrosini 15' | ||||||
| 33 | Roma | 1–1 | Milan | |||
| Zago 11' | Shevchenko 83' (pen.) | |||||
| 34 | Milan | 4–0 | Udinese | |||
| Bierhoff 11' Shevchenko 39' (pen.) West 59' Leonardo 85' |
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