| 3. Round | 12/09/2009 | AS Livorno | - | AC Milan | 0:0 | ||||
| 4. Round | 20/09/2009 | AC Milan | - | Bologna FC | 1:0 | ||||
| 5. Round | 23/09/2009 | Udinese Calcio | - | AC Milan | 1:0 | ||||
| 6. Round | 27/09/2009 | AC Milan | - | AS Bari | 0:0 | ||||
| 8. Round | 18/10/2009 | AC Milan | - | AS Roma | 2:1 | ||||
| 9. Round | 25/10/2009 | Chievo Verona | - | AC Milan | 1:2 | ||||
| 11. Round | 31/10/2009 | AC Milan | - | Parma FC | 2:0 | ||||
| 12. Round | 08/11/2009 | Lazio Roma | - | AC Milan | 1:2 | ||||
| 13. Round | 22/11/2009 | AC Milan | - | Cagliari Calcio | 4:3 | ||||
| 28. Round | 14/03/2010 | AC Milan | - | Chievo Verona | 1:0 | ||||
| 29. Round | 21/03/2010 | AC Milan | - | SSC Napoli | 1:1 | ||||
| 32. Round | 03/04/2010 | Cagliari Calcio | - | AC Milan | 2:3 | ||||
| 34. Round | 18/04/2010 | Sampdoria | - | AC Milan | 2:1 | ||||
| 35. Round | 24/04/2010 | US Palermo | - | AC Milan | 3:1 |
Italy