| 1. Round | 13/09/1959 | Real Valladolid | - | Real Zaragoza | 2:1 | ||||
| 2. Round | 20/09/1959 | Athletic Club | - | Real Valladolid | 4:3 | ||||
| 3. Round | 27/09/1959 | Real Valladolid | - | Elche CF | 1:0 | ||||
| 4. Round | 04/10/1959 | CA Osasuna | - | Real Valladolid | 4:1 | ||||
| 6. Round | 18/10/1959 | Sevilla FC | - | Real Valladolid | 5:0 | ||||
| 17. Round | 10/01/1960 | Real Valladolid | - | Athletic Club | 2:2 | ||||
| 19. Round | 24/01/1960 | Real Valladolid | - | CA Osasuna | 5:1 | ||||
| 20. Round | 31/01/1960 | Atlético Madrid | - | Real Valladolid | 2:3 |  |
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| 21. Round | 07/02/1960 | Real Valladolid | - | Sevilla FC | 3:1 | ||||
| 22. Round | 14/02/1960 | Real Oviedo | - | Real Valladolid | 2:1 | ||||
| 23. Round | 21/02/1960 | Real Valladolid | - | FC Barcelona | 1:4 | ||||
| 24. Round | 28/02/1960 | UD Las Palmas | - | Real Valladolid | 4:0 | ||||
| 26. Round | 20/03/1960 | Real Valladolid | - | Real Sociedad | 4:1 | ||||
| 27. Round | 27/03/1960 | Real Madrid | - | Real Valladolid | 1:0 | ||||
| 28. Round | 03/04/1960 | Real Valladolid | - | Real Betis | 0:1 | ||||
| 29. Round | 10/04/1960 | Valencia CF | - | Real Valladolid | 1:0 | ||||
| 30. Round | 17/04/1960 | Real Valladolid | - | Espanyol Barcelona | 1:1 |
Spain