| 1. Round | 11/08/2023 | Roda JC Kerkrade | - | Helmond Sport | 4:1 | ||||
| 2. Round | 18/08/2023 | Helmond Sport | - | FC Den Bosch | 1:0 | ||||
| 4. Round | 01/09/2023 | Helmond Sport | - | SC Cambuur | 2:1 | ||||
| 6. Round | 15/09/2023 | Helmond Sport | - | TOP Oss | 1:1 |  |
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| 5. Round | 18/09/2023 | De Graafschap | - | Helmond Sport | 2:1 | ||||
| 8. Round | 01/10/2023 | VVV-Venlo | - | Helmond Sport | 0:4 | ||||
| 27. Round | 23/02/2024 | FC Groningen | - | Helmond Sport | 0:0 | ||||
| 29. Round | 08/03/2024 | FC Utrecht (J) | - | Helmond Sport | 0:1 | ||||
| 31. Round | 11/03/2024 | Helmond Sport | - | AZ Alkmaar (J) | 3:1 |
Colombia