| 2. Round | 14/09/2008 | Genoa CFC | - | AC Milan | 2:0 | ||||
| 3. Round | 21/09/2008 | AC Milan | - | Lazio Roma | 4:1 | ||||
| 4. Round | 24/09/2008 | Reggina Calcio | - | AC Milan | 1:2 |  |
|||
| 7. Round | 19/10/2008 | AC Milan | - | Sampdoria | 3:0 | ||||
| 8. Round | 26/10/2008 | Atalanta | - | AC Milan | 0:1 | ||||
| 10. Round | 02/11/2008 | AC Milan | - | SSC Napoli | 1:0 | ||||
| 11. Round | 09/11/2008 | US Lecce | - | AC Milan | 1:1 |
Italy
