| 1. Round | 28/08/1999 | US Lecce | - | AC Milan | 2:2 |  |
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| 2. Round | 11/09/1999 | AC Milan | - | AC Perugia | 3:1 | ||||
| 3. Round | 17/09/1999 | AS Bari | - | AC Milan | 1:1 | ||||
| 4. Round | 24/09/1999 | AC Milan | - | Bologna FC | 4:0 | |
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| 5. Round | 02/10/1999 | Lazio Roma | - | AC Milan | 4:4 | ||||
| 6. Round | 16/10/1999 | AC Milan | - | Cagliari Calcio | 2:2 | ||||
| 7. Round | 22/10/1999 | Inter | - | AC Milan | 1:2 | |
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| 8. Round | 30/10/1999 | Hellas Verona | - | AC Milan | 0:0 | ||||
| 9. Round | 06/11/1999 | AC Milan | - | AC Venezia | 3:0 | |
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| 10. Round | 20/11/1999 | Juventus | - | AC Milan | 3:1 |
Liberia
