| 1. Jornada | 11.08.2023 | Roda JC Kerkrade | - | Helmond Sport | 4:1 |  |
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| 3. Jornada | 28.08.2023 | Jong PSV | - | Helmond Sport | 2:1 | ||||
| 4. Jornada | 01.09.2023 | Helmond Sport | - | SC Cambuur | 2:1 | ||||
| 6. Jornada | 15.09.2023 | Helmond Sport | - | TOP Oss | 1:1 | ||||
| 5. Jornada | 18.09.2023 | De Graafschap | - | Helmond Sport | 2:1 | ||||
| 8. Jornada | 01.10.2023 | VVV-Venlo | - | Helmond Sport | 0:4 | ||||
| 11. Jornada | 20.10.2023 | FC Eindhoven | - | Helmond Sport | 1:2 | ||||
| 16. Jornada | 24.11.2023 | Helmond Sport | - | FC Emmen | 1:2 |
Países Bajos