| 4. Round | 07/09/2018 | FC Utrecht (J) | - | Jong PSV | 3:2 | ||||
| 9. Round | 15/10/2018 | Jong PSV | - | Jong Ajax | 2:1 | ||||
| 12. Round | 05/11/2018 | Jong PSV | - | FC Den Bosch | 0:1 | ||||
| 17. Round | 10/12/2018 | Jong PSV | - | SC Cambuur | 1:2 | ||||
| 24. Round | 08/02/2019 | FC Eindhoven | - | Jong PSV | 1:2 |  |
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| 26. Round | 22/02/2019 | Jong PSV | - | Roda JC Kerkrade | 2:2 | ||||
| 27. Round | 01/03/2019 | Helmond Sport | - | Jong PSV | 0:2 | ||||
| 28. Round | 08/03/2019 | Jong PSV | - | FC Utrecht (J) | 3:1 | ||||
| 29. Round | 15/03/2019 | SC Cambuur | - | Jong PSV | 3:1 | ||||
| 34. Round | 12/04/2019 | FC Volendam | - | Jong PSV | 0:3 | ||||
| 35. Round | 19/04/2019 | Go Ahead Eagles | - | Jong PSV | 2:1 | ||||
| 38. Round | 03/05/2019 | Jong PSV | - | Telstar | 2:0 |
Netherlands