| 2. Round | 16/08/2019 | Almere City FC | - | Jong PSV | 3:2 | ||||
| 3. Round | 26/08/2019 | Jong PSV | - | MVV | 0:1 | ||||
| 4. Round | 30/08/2019 | FC Utrecht (J) | - | Jong PSV | 3:0 |  |
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| 8. Round | 27/09/2019 | SBV Excelsior | - | Jong PSV | 5:2 | ||||
| 9. Round | 04/10/2019 | Jong PSV | - | FC Volendam | 3:1 | ||||
| 11. Round | 18/10/2019 | NEC Nijmegen | - | Jong PSV | 1:0 | ||||
| 12. Round | 25/10/2019 | TOP Oss | - | Jong PSV | 1:0 | ||||
| 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 | |
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| 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 | ||||
| 21. Round | 13/01/2020 | Jong PSV | - | Jong Ajax | 0:0 | ||||
| 22. Round | 17/01/2020 | FC Volendam | - | Jong PSV | 4:2 | ||||
| 24. Round | 31/01/2020 | MVV | - | Jong PSV | 3:1 | ||||
| 26. Round | 14/02/2020 | FC Eindhoven | - | Jong PSV | 1:1 |
Netherlands