| 1. Round | 17/08/2018 | Jong PSV | - | FC Eindhoven | 2:1 | ||||
| 2. Round | 24/08/2018 | TOP Oss | - | Jong PSV | 4:1 | ||||
| 3. Round | 31/08/2018 | Jong PSV | - | Helmond Sport | 1:1 | ||||
| 5. Round | 14/09/2018 | NEC Nijmegen | - | Jong PSV | 4:4 | ||||
| 6. Round | 21/09/2018 | Jong PSV | - | FC Volendam | 1:0 | ||||
| 7. Round | 30/09/2018 | FC Twente | - | Jong PSV | 2:1 | ||||
| 8. Round | 05/10/2018 | Roda JC Kerkrade | - | Jong PSV | 2:3 | ||||
| 10. Round | 19/10/2018 | MVV | - | Jong PSV | 2:2 | ||||
| 11. Round | 26/10/2018 | Jong PSV | - | FC Dordrecht | 2:2 | ||||
| 13. Round | 09/11/2018 | RKC Waalwijk | - | Jong PSV | 3:5 | ||||
| 14. Round | 17/11/2018 | Jong PSV | - | AZ Alkmaar (J) | 3:1 | ||||
| 15. Round | 23/11/2018 | Sparta Rotterdam | - | Jong PSV | 0:0 | ||||
| 16. Round | 03/12/2018 | Jong PSV | - | Go Ahead Eagles | 5:1 | ||||
| 18. Round | 14/12/2018 | Telstar | - | Jong PSV | 2:4 | ||||
| 19. Round | 21/12/2018 | Jong PSV | - | Almere City FC | 5:2 |
Netherlands