| 1. Round | 15/09/1999 | Zenit St. Petersburg | - | Bologna FC | 0:3 | ||||
| 1. Round | 29/09/1999 | Bologna FC | - | Zenit St. Petersburg | 2:2 |  |
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| 2. Round | 01/11/1999 | Bologna FC | - | RSC Anderlecht | 3:0 | ||||
| 3. Round | 22/11/1999 | Bologna FC | - | Galatasaray | 1:1 | ||||
| 3. Round | 08/12/1999 | Galatasaray | - | Bologna FC | 2:1 |
Sweden