| 2. Round | 08/09/1998 | Calcio Padova | - | ACF Fiorentina | 0:1 | ||||
| 2. Round | 22/09/1998 | ACF Fiorentina | - | Calcio Padova | 2:0 | ||||
| Round of 16 | 27/10/1998 | ACF Fiorentina | - | US Lecce | 1:0 |  |
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| Round of 16 | 09/11/1998 | US Lecce | - | ACF Fiorentina | 0:4 | ||||
| Quarter-finals | 01/12/1998 | Atalanta | - | ACF Fiorentina | 3:2 | ||||
| Semi-finals | 17/02/1999 | Bologna FC | - | ACF Fiorentina | 0:2 | ||||
| Semi-finals | 09/03/1999 | ACF Fiorentina | - | Bologna FC | 2:2 aet |
Spain