| 21. Round | 13/01/2020 | AZ Alkmaar (J) | - | TOP Oss | 3:1 |  |
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| 22. Round | 17/01/2020 | TOP Oss | - | SC Cambuur | 3:2 | |
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| 23. Round | 24/01/2020 | Telstar | - | TOP Oss | 1:0 | ||||
| 24. Round | 31/01/2020 | TOP Oss | - | Roda JC Kerkrade | 0:0 | ||||
| 25. Round | 07/02/2020 | NAC Breda | - | TOP Oss | 1:1 | ||||
| 27. Round | 21/02/2020 | Jong PSV | - | TOP Oss | 1:1 | |
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| 28. Round | 28/02/2020 | TOP Oss | - | FC Utrecht (J) | 2:1 | ||||
| 29. Round | 06/03/2020 | FC Eindhoven | - | TOP Oss | 2:2 |
Netherlands