| 5. Round | 14/09/2018 | NEC Nijmegen | - | Jong PSV | 4:4 |  |
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| 14. Round | 17/11/2018 | Jong PSV | - | AZ Alkmaar (J) | 3:1 | |
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| 17. Round | 10/12/2018 | Jong PSV | - | SC Cambuur | 1:2 | ||||
| 24. Round | 08/02/2019 | FC Eindhoven | - | Jong PSV | 1:2 | ||||
| 29. Round | 15/03/2019 | SC Cambuur | - | Jong PSV | 3:1 | ||||
| 32. Round | 01/04/2019 | FC Den Bosch | - | Jong PSV | 3:1 | ||||
| 34. Round | 12/04/2019 | FC Volendam | - | Jong PSV | 0:3 | |
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| 36. Round | 22/04/2019 | Jong PSV | - | Sparta Rotterdam | 2:0 | ||||
| 38. Round | 03/05/2019 | Jong PSV | - | Telstar | 2:0 |
Netherlands