| 1. Round | 11/08/2019 | Sportfreunde Siegen | - | Holzwickeder SC | 3:3 | ||||
| 2. Round | 18/08/2019 | Holzwickeder SC | - | SV Schermbeck 1912 | 0:1 | ||||
| 6. Round | 15/09/2019 | FCE Rheine | - | Holzwickeder SC | 2:4 | ||||
| 8. Round | 29/09/2019 | Westfalia Rhynern | - | Holzwickeder SC | 3:0 | ||||
| 9. Round | 06/10/2019 | Holzwickeder SC | - | 1. FC Kaan-Marienborn | 2:1 | ||||
| 10. Round | 13/10/2019 | SC Wiedenbrück | - | Holzwickeder SC | 4:2 | ||||
| 11. Round | 16/10/2019 | Holzwickeder SC | - | ASC 09 Dortmund | 1:3 | ||||
| 12. Round | 27/10/2019 | FC Gütersloh | - | Holzwickeder SC | 0:1 | ||||
| 13. Round | 03/11/2019 | Holzwickeder SC | - | TSG Sprockhövel | 2:1 |  |
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| 15. Round | 17/11/2019 | Holzwickeder SC | - | TuS Erndtebrück | 7:1 | ||||
| 16. Round | 01/12/2019 | Rot Weiss Ahlen | - | Holzwickeder SC | 1:2 | |
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| 17. Round | 08/12/2019 | Holzwickeder SC | - | Hammer SpVg | 4:2 | ||||
| 18. Round | 22/02/2020 | Holzwickeder SC | - | Sportfreunde Siegen | 0:0 | ||||
| 21. Round | 01/03/2020 | SC Paderborn 07 II | - | Holzwickeder SC | 3:2 | ||||
| 22. Round | 08/03/2020 | Preußen Münster II | - | Holzwickeder SC | 1:3 |
Germany