| 1. Round | 15/09/1998 | Sporting CP | - | Bologna FC | 0:2 | ||||
| 1. Round | 29/09/1998 | Bologna FC | - | Sporting CP | 2:1 |  |
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| 2. Round | 20/10/1998 | Bologna FC | - | Slavia Praha | 2:1 | |
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| 2. Round | 03/11/1998 | Slavia Praha | - | Bologna FC | 0:2 | |
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| Round of 16 | 24/11/1998 | Bologna FC | - | Real Betis | 4:1 | ||||
| Round of 16 | 08/12/1998 | Real Betis | - | Bologna FC | 1:0 | ||||
| Quarter-finals | 02/03/1999 | Bologna FC | - | Olympique Lyonnais | 3:0 | |
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| Quarter-finals | 16/03/1999 | Olympique Lyonnais | - | Bologna FC | 2:0 |  |
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| Semi-finals | 06/04/1999 | Olympique Marseille | - | Bologna FC | 0:0 | ||||
| Semi-finals | 20/04/1999 | Bologna FC | - | Olympique Marseille | 1:1 |
Italy