| 1. Jornada | 11.08.2023 | Roda JC Kerkrade | - | Helmond Sport | 4:1 | ||||
| 2. Jornada | 18.08.2023 | Helmond Sport | - | FC Den Bosch | 1:0 | ||||
| 4. Jornada | 01.09.2023 | Helmond Sport | - | SC Cambuur | 2:1 | ||||
| 6. Jornada | 15.09.2023 | Helmond Sport | - | TOP Oss | 1:1 |  |
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| 5. Jornada | 18.09.2023 | De Graafschap | - | Helmond Sport | 2:1 | ||||
| 8. Jornada | 01.10.2023 | VVV-Venlo | - | Helmond Sport | 0:4 | ||||
| 27. Jornada | 23.02.2024 | FC Groningen | - | Helmond Sport | 0:0 | ||||
| 29. Jornada | 08.03.2024 | FC Utrecht (J) | - | Helmond Sport | 0:1 | ||||
| 31. Jornada | 11.03.2024 | Helmond Sport | - | AZ Alkmaar (J) | 3:1 |
Colombia