| 21. Round | 24/02/2019 | Holzwickeder SC | - | Sportfreunde Siegen | 0:0 | ||||
| 24. Round | 24/03/2019 | Holzwickeder SC | - | Rot Weiss Ahlen | 3:2 | ||||
| 19. Round | 27/03/2019 | Holzwickeder SC | - | TuS Erndtebrück | 4:3 | ||||
| 25. Round | 31/03/2019 | Westfalia Rhynern | - | Holzwickeder SC | 2:1 | ||||
| 26. Round | 07/04/2019 | Holzwickeder SC | - | ASC 09 Dortmund | 1:2 | ||||
| 27. Round | 14/04/2019 | Westfalia Herne | - | Holzwickeder SC | 2:0 | ||||
| 28. Round | 18/04/2019 | Holzwickeder SC | - | FCE Rheine | 4:3 | ||||
| 30. Round | 28/04/2019 | Holzwickeder SC | - | FC Schalke 04 II | 2:2 | ||||
| 22. Round | 01/05/2019 | Holzwickeder SC | - | 1. FC Gievenbeck | 4:1 | ||||
| 31. Round | 05/05/2019 | TuS Haltern | - | Holzwickeder SC | 1:1 | ||||
| 32. Round | 12/05/2019 | Holzwickeder SC | - | TuS Ennepetal | 3:1 |  |
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| 23. Round | 15/05/2019 | FC Gütersloh | - | Holzwickeder SC | 2:0 | |
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| 33. Round | 19/05/2019 | Hammer SpVg | - | Holzwickeder SC | 3:0 | ||||
| 34. Round | 26/05/2019 | Holzwickeder SC | - | FC Brünninghausen | 3:0 |
???