| 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 |
| 1998-12-20 | SampdoriavMilanSerie A · Italy | 2–2 | Serie A · Italy |
| 1998-12-13 | MilanvVicenzaSerie A · Italy | 1–0 | Serie A · Italy |
| 1998-12-06 | MilanvUdineseSerie A · Italy | 3–0 | Serie A · Italy |
| 1998-11-29 | ParmavMilanSerie A · Italy | 4–0 | Serie A · Italy |
| 1998-11-22 | MilanvLazioSerie A · Italy | 1–0 | Serie A · Italy |
| 1998-11-15 | BarivMilanSerie A · Italy | 0–0 | Serie A · Italy |
| 1998-11-08 | MilanvInterSerie A · Italy | 2–2 | Serie A · Italy |
| 1998-11-01 | PiacenzavMilanSerie A · Italy | 1–1 | Serie A · Italy |
| 1998-10-25 | MilanvRomaSerie A · Italy | 3–2 | Serie A · Italy |
| 1998-10-18 | CagliarivMilanSerie A · Italy | 1–0 | Serie A · Italy |
| 1998-10-04 | VeneziavMilanSerie A · Italy | 0–2 | Serie A · Italy |
| 1998-09-26 | MilanvFiorentinaSerie A · Italy | 1–3 | Serie A · Italy |
| 1998-09-20 | SalernitanavMilanSerie A · Italy | 1–2 | Serie A · Italy |
| 1998-09-12 | MilanvBolognaSerie A · Italy | 3–0 | Serie A · Italy |
| 1998-05-16 | FiorentinavMilanSerie A · Italy | 2–0 | Serie A · Italy |
| 1998-05-10 | MilanvParmaSerie A · Italy | 1–1 | Serie A · Italy |
| 1998-05-03 | RomavMilanSerie A · Italy | 5–0 | Serie A · Italy |
| 1998-04-26 | MilanvNapoliSerie A · Italy | 0–0 | Serie A · Italy |
| 1998-04-19 | BolognavMilanSerie A · Italy | 3–0 | Serie A · Italy |
| 1998-04-11 | MilanvAtalantaSerie A · Italy | 3–0 | Serie A · Italy |
| 1998-04-05 | BarivMilanSerie A · Italy | 1–0 | Serie A · Italy |
| 1998-03-28 | JuventusvMilanSerie A · Italy | 4–1 | Serie A · Italy |
| 1998-03-22 | MilanvInterSerie A · Italy | 0–3 | Serie A · Italy |
| 1998-03-15 | BresciavMilanSerie A · Italy | 2–2 | Serie A · Italy |