| 3. Round | 27/10/1998 | Málaga CF | - | Real Valladolid | 1:2 | ||||
| 3. Round | 10/11/1998 | Real Valladolid | - | Málaga CF | 3:2 | ||||
| 4. Round | 12/01/1999 | CD Badajoz | - | Real Valladolid | 10:11 pso | ||||
| Round of 16 | 19/01/1999 | Espanyol Barcelona | - | Real Valladolid | 4:2 |  |
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| Round of 16 | 02/02/1999 | Real Valladolid | - | Espanyol Barcelona | 2:2 |  |
Spain