| 1. Round | 10/11/1999 | UD Salamanca | - | Rayo Vallecano | 2:2 | ||||
| 1. Round | 01/12/1999 | Rayo Vallecano | - | UD Salamanca | 4:2 |  |
|||
| 2. Round | 12/01/2000 | Rayo Vallecano | - | Athletic Club | 0:0 | ||||
| Round of 16 | 19/01/2000 | UE Lleida | - | Rayo Vallecano | 2:3 | |
|||
| Round of 16 | 02/02/2000 | Rayo Vallecano | - | UE Lleida | 3:1 | |
|||
| Quarter-finals | 09/02/2000 | Atlético Madrid | - | Rayo Vallecano | 0:0 | ||||
| Quarter-finals | 16/02/2000 | Rayo Vallecano | - | Atlético Madrid | 2:2 |
Spain