| 2. Round | 16/08/2019 | Almere City FC | - | Jong PSV | 3:2 | ||||
| 4. Round | 30/08/2019 | FC Utrecht (J) | - | Jong PSV | 3:0 | ||||
| 5. Round | 16/09/2019 | Jong Ajax | - | Jong PSV | 2:0 | ||||
| 7. Round | 23/09/2019 | Jong PSV | - | SC Cambuur | 0:1 | ||||
| 8. Round | 27/09/2019 | SBV Excelsior | - | Jong PSV | 5:2 | ||||
| 9. Round | 04/10/2019 | Jong PSV | - | FC Volendam | 3:1 | ||||
| 12. Round | 25/10/2019 | TOP Oss | - | Jong PSV | 1:0 | ||||
| 14. Round | 08/11/2019 | Jong PSV | - | Telstar | 1:1 | ||||
| 15. Round | 25/11/2019 | Jong PSV | - | NAC Breda | 1:3 | ||||
| 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 | ||||
| 24. Round | 31/01/2020 | MVV | - | Jong PSV | 3:1 |  |
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| 26. Round | 14/02/2020 | FC Eindhoven | - | Jong PSV | 1:1 | ||||
| 29. Round | 06/03/2020 | Telstar | - | Jong PSV | 1:0 |
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