| 1. Jornada | 29.08.1999 | US Lecce | - | Milan | 2:2 |  |
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| 2. Jornada | 12.09.1999 | Milan | - | AC Perugia | 3:1 | ||||
| 3. Jornada | 18.09.1999 | AS Bari | - | Milan | 1:1 | ||||
| 4. Jornada | 25.09.1999 | Milan | - | Bolonia | 4:0 | |
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| 5. Jornada | 03.10.1999 | Lazio | - | Milan | 4:4 | ||||
| 6. Jornada | 17.10.1999 | Milan | - | Cagliari Calcio | 2:2 | ||||
| 7. Jornada | 23.10.1999 | Inter | - | Milan | 1:2 | |
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| 8. Jornada | 31.10.1999 | Hellas Verona | - | Milan | 0:0 | ||||
| 9. Jornada | 07.11.1999 | Milan | - | AC Venezia | 3:0 | |
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| 10. Jornada | 21.11.1999 | Juventus | - | Milan | 3:1 |
Liberia
