| 1. Jornada | 11.08.2023 | FC Den Bosch | - | TOP Oss | 1:0 |  |
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| 2. Jornada | 18.08.2023 | TOP Oss | - | Jong PSV | 4:1 | ||||
| 3. Jornada | 25.08.2023 | Roda JC Kerkrade | - | TOP Oss | 2:0 | ||||
| 4. Jornada | 01.09.2023 | TOP Oss | - | FC Groningen | 0:2 | ||||
| 6. Jornada | 15.09.2023 | Helmond Sport | - | TOP Oss | 1:1 | |
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| 5. Jornada | 18.09.2023 | TOP Oss | - | FC Dordrecht | 0:1 | ||||
| 7. Jornada | 03.10.2023 | Willem II | - | TOP Oss | 2:1 | ||||
| 16. Jornada | 24.11.2023 | Jong Ajax | - | TOP Oss | 1:0 | ||||
| 15. Jornada | 27.11.2023 | FC Eindhoven | - | TOP Oss | 0:0 |
Grecia