| 4. Round | 26/08/2022 | Telstar | - | Helmond Sport | 2:1 |  |
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| 5. Round | 02/09/2022 | Helmond Sport | - | Almere City FC | 3:0 | ||||
| 6. Round | 09/09/2022 | FC Utrecht (J) | - | Helmond Sport | 2:0 | ||||
| 7. Round | 16/09/2022 | Helmond Sport | - | FC Dordrecht | 2:1 | |
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| 8. Round | 23/09/2022 | Heracles Almelo | - | Helmond Sport | 2:0 | |
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| 9. Round | 30/09/2022 | Helmond Sport | - | TOP Oss | 1:2 | ||||
| 10. Round | 07/10/2022 | Jong Ajax | - | Helmond Sport | 0:1 | ||||
| 11. Round | 14/10/2022 | Helmond Sport | - | Willem II | 1:3 | ||||
| 12. Round | 24/10/2022 | Jong PSV | - | Helmond Sport | 6:0 | ||||
| 13. Round | 28/10/2022 | Helmond Sport | - | ADO Den Haag | 2:1 | ||||
| 14. Round | 04/11/2022 | MVV | - | Helmond Sport | 4:0 | |
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| 15. Round | 12/11/2022 | Roda JC Kerkrade | - | Helmond Sport | 0:1 | |
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| 17. Round | 12/12/2022 | PEC Zwolle | - | Helmond Sport | 1:0 |
Netherlands