| 2. Round | 16/08/2019 | FC Volendam | - | Roda JC Kerkrade | 4:0 | ||||
| 4. Round | 30/08/2019 | FC Volendam | - | NAC Breda | 2:1 | ||||
| 6. Round | 13/09/2019 | FC Volendam | - | FC Dordrecht | 1:1 | ||||
| 9. Round | 04/10/2019 | Jong PSV | - | FC Volendam | 3:1 | ||||
| 10. Round | 13/10/2019 | FC Volendam | - | FC Den Bosch | 1:1 |  |
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| 12. Round | 25/10/2019 | FC Volendam | - | AZ Alkmaar (J) | 3:2 | ||||
| 15. Round | 15/11/2019 | TOP Oss | - | FC Volendam | 1:2 | ||||
| 16. Round | 22/11/2019 | SBV Excelsior | - | FC Volendam | 1:2 | ||||
| 18. Round | 06/12/2019 | FC Eindhoven | - | FC Volendam | 1:4 |
Netherlands