| 1. Round | 06/09/1988 | Vitosha Sofia | - | AC Milan | 0:2 | ||||
| 1. Round | 06/10/1988 | AC Milan | - | Vitosha Sofia | 5:2 | ||||
| Round of 16 | 25/10/1988 | AC Milan | - | Crvena Zvezda | 1:1 | ||||
| Round of 16 | 09/11/1988 | Crvena Zvezda | - | AC Milan | 2:4 pso | ||||
| Quarter-finals | 28/02/1989 | Werder Bremen | - | AC Milan | 0:0 | ||||
| Quarter-finals | 14/03/1989 | AC Milan | - | Werder Bremen | 1:0 | ||||
| Semi-finals | 04/04/1989 | Real Madrid | - | AC Milan | 1:1 | ||||
| Semi-finals | 18/04/1989 | AC Milan | - | Real Madrid | 5:0 |  |
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| Final | 24/05/1989 | AC Milan | - | CSA Steaua București | 4:0 |
Italy
