| 1. Round | 17/08/2018 | Roda JC Kerkrade | - | Jong Ajax | 2:1 | ||||
| 2. Round | 24/08/2018 | Jong Ajax | - | FC Dordrecht | 5:2 |  |
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| 5. Round | 17/09/2018 | Jong Ajax | - | Helmond Sport | 2:0 |  |
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| 6. Round | 21/09/2018 | Go Ahead Eagles | - | Jong Ajax | 2:1 | |
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| 7. Round | 28/09/2018 | Jong Ajax | - | FC Eindhoven | 0:3 | ||||
| 11. Round | 26/10/2018 | FC Volendam | - | Jong Ajax | 3:1 | ||||
| 12. Round | 02/11/2018 | SC Cambuur | - | Jong Ajax | 2:1 | |
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| 13. Round | 09/11/2018 | Jong Ajax | - | NEC Nijmegen | 4:0 | |
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| 15. Round | 23/11/2018 | Jong Ajax | - | MVV | 0:1 | ||||
| 17. Round | 07/12/2018 | Jong Ajax | - | TOP Oss | 1:0 | |
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| 18. Round | 14/12/2018 | Almere City FC | - | Jong Ajax | 2:3 | ||||
| 19. Round | 21/12/2018 | Jong Ajax | - | Sparta Rotterdam | 2:0 | |
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| 21. Round | 18/01/2019 | RKC Waalwijk | - | Jong Ajax | 4:1 | ||||
| 25. Round | 15/02/2019 | FC Eindhoven | - | Jong Ajax | 1:1 | ||||
| 26. Round | 22/02/2019 | Telstar | - | Jong Ajax | 0:2 | |
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| 28. Round | 11/03/2019 | Jong Ajax | - | AZ Alkmaar (J) | 1:1 | ||||
| 37. Round | 26/04/2019 | Sparta Rotterdam | - | Jong Ajax | 2:2 | ||||
| 38. Round | 03/05/2019 | Jong Ajax | - | Almere City FC | 8:0 | |
Netherlands