| 1. Round | 12/08/2019 | Jong PSV | - | FC Den Bosch | 2:2 |  |
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| 3. Round | 26/08/2019 | Jong PSV | - | MVV | 0:1 |  |
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| 13. Round | 04/11/2019 | Jong PSV | - | Roda JC Kerkrade | 1:1 | ||||
| 14. Round | 08/11/2019 | Jong PSV | - | Telstar | 1:1 | ||||
| 16. Round | 22/11/2019 | De Graafschap | - | Jong PSV | 4:1 | ||||
| 15. Round | 25/11/2019 | Jong PSV | - | NAC Breda | 1:3 | ||||
| 17. Round | 29/11/2019 | Helmond Sport | - | Jong PSV | 2:3 | ||||
| 18. Round | 06/12/2019 | Go Ahead Eagles | - | Jong PSV | 1:1 | ||||
| 19. Round | 13/12/2019 | Jong PSV | - | FC Dordrecht | 0:1 | ||||
| 20. Round | 20/12/2019 | FC Den Bosch | - | Jong PSV | 2:1 | ||||
| 22. Round | 17/01/2020 | FC Volendam | - | Jong PSV | 4:2 | ||||
| 23. Round | 27/01/2020 | Jong PSV | - | SBV Excelsior | 2:1 | ||||
| 28. Round | 28/02/2020 | SC Cambuur | - | Jong PSV | 4:2 | ||||
| 29. Round | 06/03/2020 | Telstar | - | Jong PSV | 1:0 |
Netherlands