| 1. Round | 29/08/1998 | CF Extremadura | - | Real Valladolid | 0:0 | ||||
| 2. Round | 11/09/1998 | Real Valladolid | - | Real Madrid | 0:1 | ||||
| 3. Round | 19/09/1998 | RC Celta | - | Real Valladolid | 0:0 | ||||
| 4. Round | 25/09/1998 | Real Valladolid | - | Valencia CF | 3:1 | ||||
| 5. Round | 03/10/1998 | UD Salamanca | - | Real Valladolid | 1:0 | ||||
| 19. Round | 23/01/1999 | Real Valladolid | - | Racing Santander | 0:0 |
Serbia