| 2. Round | 09/09/1998 | Ravenna Calcio | - | Juventus | 0:2 | ||||
| 2. Round | 22/09/1998 | Juventus | - | Ravenna Calcio | 4:0 | ||||
| Round of 16 | 26/10/1998 | Juventus | - | AC Venezia | 1:1 | ||||
| Round of 16 | 10/11/1998 | AC Venezia | - | Juventus | 2:2 aet | ||||
| Quarter-finals | 12/01/1999 | Juventus | - | Bologna FC | 1:2 |  |
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| Quarter-finals | 25/01/1999 | Bologna FC | - | Juventus | 0:1 |
England