| 1. Round | 18/09/2008 | AC Milan | - | FC Zürich | 3:1 | ||||
| 1. Round | 02/10/2008 | FC Zürich | - | AC Milan | 0:1 | ||||
| Group E | 23/10/2008 | sc Heerenveen | - | AC Milan | 1:3 | ||||
| Group E | 06/11/2008 | AC Milan | - | Sporting Braga | 1:0 | ||||
| Group E | 27/11/2008 | Portsmouth FC | - | AC Milan | 2:2 | ||||
| Group E | 17/12/2008 | AC Milan | - | VfL Wolfsburg | 2:2 | ||||
| 3. Round | 18/02/2009 | Werder Bremen | - | AC Milan | 1:1 | ||||
| 3. Round | 26/02/2009 | AC Milan | - | Werder Bremen | 2:2 |
Brazil