| 2. Round | 19/08/2019 | Jong Ajax | - | NEC Nijmegen | 3:3 | ||||
| 4. Round | 30/08/2019 | Jong Ajax | - | Almere City FC | 3:2 | ||||
| 5. Round | 16/09/2019 | Jong Ajax | - | Jong PSV | 2:0 | ||||
| 7. Round | 20/09/2019 | Go Ahead Eagles | - | Jong Ajax | 1:1 | ||||
| 9. Round | 04/10/2019 | Jong Ajax | - | FC Eindhoven | 6:0 | ||||
| 12. Round | 25/10/2019 | SBV Excelsior | - | Jong Ajax | 1:3 | ||||
| 13. Round | 04/11/2019 | Jong Ajax | - | FC Volendam | 1:3 | ||||
| 15. Round | 25/11/2019 | Jong Ajax | - | Helmond Sport | 1:1 | ||||
| 17. Round | 29/11/2019 | Telstar | - | Jong Ajax | 2:3 | ||||
| 20. Round | 20/12/2019 | Jong Ajax | - | TOP Oss | 2:0 | ||||
| 24. Round | 03/02/2020 | Jong Ajax | - | Go Ahead Eagles | 5:1 | ||||
| 26. Round | 17/02/2020 | Jong Ajax | - | NAC Breda | 2:4 | ||||
| 29. Round | 06/03/2020 | FC Volendam | - | Jong Ajax | 4:0 |
Croatia