| 1. Round | 09/08/2019 | TOP Oss | - | Jong Ajax | 2:1 | ||||
| 2. Round | 19/08/2019 | Jong Ajax | - | NEC Nijmegen | 3:3 | ||||
| 3. Round | 23/08/2019 | FC Dordrecht | - | Jong Ajax | 2:5 | ||||
| 4. Round | 30/08/2019 | Jong Ajax | - | Almere City FC | 3:2 | ||||
| 8. Round | 27/09/2019 | MVV | - | Jong Ajax | 1:4 | ||||
| 9. Round | 04/10/2019 | Jong Ajax | - | FC Eindhoven | 6:0 | ||||
| 16. Round | 22/11/2019 | NAC Breda | - | Jong Ajax | 1:2 | ||||
| 15. Round | 25/11/2019 | Jong Ajax | - | Helmond Sport | 1:1 | ||||
| 18. Round | 09/12/2019 | Jong Ajax | - | Roda JC Kerkrade | 2:0 | ||||
| 19. Round | 13/12/2019 | SC Cambuur | - | Jong Ajax | 0:2 | ||||
| 20. Round | 20/12/2019 | Jong Ajax | - | TOP Oss | 2:0 | ||||
| 22. Round | 20/01/2020 | Jong Ajax | - | FC Dordrecht | 2:0 | ||||
| 23. Round | 24/01/2020 | NEC Nijmegen | - | Jong Ajax | 3:3 | ||||
| 24. Round | 03/02/2020 | Jong Ajax | - | Go Ahead Eagles | 5:1 | ||||
| 25. Round | 10/02/2020 | FC Utrecht (J) | - | Jong Ajax | 7:2 | ||||
| 26. Round | 17/02/2020 | Jong Ajax | - | NAC Breda | 2:4 | ||||
| 27. Round | 21/02/2020 | Helmond Sport | - | Jong Ajax | 0:2 | ||||
| 28. Round | 28/02/2020 | Jong Ajax | - | Telstar | 2:2 |  |
|||
| 29. Round | 06/03/2020 | FC Volendam | - | Jong Ajax | 4:0 |
Netherlands