| 6. Round | 13/09/2019 | De Graafschap | - | Jong Ajax | 3:2 | ||||
| 7. Round | 20/09/2019 | Go Ahead Eagles | - | Jong Ajax | 1:1 | ||||
| 8. Round | 27/09/2019 | MVV | - | Jong Ajax | 1:4 | ||||
| 9. Round | 04/10/2019 | Jong Ajax | - | FC Eindhoven | 6:0 | ||||
| 11. Round | 18/10/2019 | AZ Alkmaar (J) | - | Jong Ajax | 3:2 | ||||
| 10. Round | 21/10/2019 | Jong Ajax | - | FC Utrecht (J) | 4:0 | ||||
| 12. Round | 25/10/2019 | SBV Excelsior | - | Jong Ajax | 1:3 | ||||
| 13. Round | 04/11/2019 | Jong Ajax | - | FC Volendam | 1:3 | ||||
| 14. Round | 08/11/2019 | Jong Ajax | - | FC Den Bosch | 5:1 | ||||
| 17. Round | 29/11/2019 | Telstar | - | Jong Ajax | 2:3 |  |
 |
||
| 18. Round | 09/12/2019 | Jong Ajax | - | Roda JC Kerkrade | 2:0 | ||||
| 19. Round | 13/12/2019 | SC Cambuur | - | Jong Ajax | 0:2 | |
Netherlands