| 1999-12-19 | MilanvRegginaSerie A · Italy | 2–2 | Serie A · Italy |
| 1999-12-11 | MilanvTorinoSerie A · Italy | 2–0 | Serie A · Italy |
| 1999-12-05 | FiorentinavMilanSerie A · Italy | 2–1 | Serie A · Italy |
| 1999-11-28 | MilanvParmaSerie A · Italy | 2–1 | Serie A · Italy |
| 1999-11-21 | JuventusvMilanSerie A · Italy | 3–1 | Serie A · Italy |
| 1999-11-07 | MilanvVeneziaSerie A · Italy | 3–0 | Serie A · Italy |
| 1999-10-31 | VeronavMilanSerie A · Italy | 0–0 | Serie A · Italy |
| 1999-10-23 | IntervMilanSerie A · Italy | 1–2 | Serie A · Italy |
| 1999-10-17 | MilanvCagliariSerie A · Italy | 2–2 | Serie A · Italy |
| 1999-10-03 | LaziovMilanSerie A · Italy | 4–4 | Serie A · Italy |
| 1999-09-25 | MilanvBolognaSerie A · Italy | 4–0 | Serie A · Italy |
| 1999-09-18 | BarivMilanSerie A · Italy | 1–1 | Serie A · Italy |
| 1999-09-12 | MilanvPerugiaSerie A · Italy | 3–1 | Serie A · Italy |
| 1999-08-29 | LeccevMilanSerie A · Italy | 2–2 | Serie A · Italy |
| 1999-05-23 | PerugiavMilanSerie A · Italy | 1–2 | Serie A · Italy |
| 1999-05-15 | MilanvEmpoliSerie A · Italy | 4–0 | Serie A · Italy |
| 1999-05-09 | JuventusvMilanSerie A · Italy | 0–2 | Serie A · Italy |
| 1999-05-02 | MilanvSampdoriaSerie A · Italy | 3–2 | Serie A · Italy |
| 1999-04-25 | VicenzavMilanSerie A · Italy | 0–2 | Serie A · Italy |
| 1999-04-18 | UdinesevMilanSerie A · Italy | 1–5 | Serie A · Italy |
| 1999-04-11 | MilanvParmaSerie A · Italy | 2–1 | Serie A · Italy |
| 1999-04-03 | LaziovMilanSerie A · Italy | 0–0 | Serie A · Italy |
| 1999-03-21 | MilanvBariSerie A · Italy | 2–2 | Serie A · Italy |
| 1999-03-13 | IntervMilanSerie A · Italy | 2–2 | Serie A · Italy |
| 1999-03-07 | MilanvPiacenzaSerie A · Italy | 1–0 | Serie A · Italy |
| 1999-02-27 | RomavMilanSerie A · Italy | 1–0 | Serie A · Italy |
| 1999-02-21 | MilanvCagliariSerie A · Italy | 1–0 | Serie A · Italy |
| 1999-02-14 | MilanvVeneziaSerie A · Italy | 2–1 | Serie A · Italy |
| 1999-02-07 | FiorentinavMilanSerie A · Italy | 0–0 | Serie A · Italy |
| 1999-01-31 | MilanvSalernitanaSerie A · Italy | 3–2 | Serie A · Italy |
| 1999-01-24 | BolognavMilanSerie A · Italy | 2–3 | Serie A · Italy |
| 1999-01-17 | MilanvPerugiaSerie A · Italy | 2–1 | Serie A · Italy |
| 1999-01-10 | EmpolivMilanSerie A · Italy | 1–1 | Serie A · Italy |
| 1999-01-06 | MilanvJuventusSerie A · Italy | 1–1 | Serie A · Italy |