| 1. Round | 25/08/2019 | Las Rozas CF | - | Real Madrid Castilla | 1:1 | ||||
| 8. Round | 12/10/2019 | Real Madrid Castilla | - | Pontevedra CF | 2:1 |  |
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| 13. Round | 17/11/2019 | Atlético Baleares | - | Real Madrid Castilla | 1:1 | |
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| 14. Round | 23/11/2019 | Real Madrid Castilla | - | Real Oviedo B | 2:0 | ||||
| 15. Round | 30/11/2019 | Atlético Madrid B | - | Real Madrid Castilla | 2:0 | ||||
| 16. Round | 07/12/2019 | Real Madrid Castilla | - | CF Internacional | 2:2 | ||||
| 17. Round | 15/12/2019 | Real Madrid Castilla | - | Getafe CF B | 3:0 | |
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| 19. Round | 05/01/2020 | Real Madrid Castilla | - | UD Melilla | 1:2 | ||||
| 18. Round | 08/01/2020 | RC Celta B | - | Real Madrid Castilla | 0:1 | |
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| 20. Round | 12/01/2020 | Real Madrid Castilla | - | Las Rozas CF | 2:2 | ||||
| 21. Round | 19/01/2020 | Marino de Luanco | - | Real Madrid Castilla | 1:0 | |
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| 23. Round | 02/02/2020 | UP Langreo | - | Real Madrid Castilla | 1:1 | ||||
| 25. Round | 16/02/2020 | Rayo Majadahonda | - | Real Madrid Castilla | 2:2 | ||||
| 28. Round | 07/03/2020 | Real Madrid Castilla | - | Coruxo FC | 4:0 | |
Spain