1. Round | 11/08/2019 | Sportfreunde Siegen | - | Holzwickeder SC | 3:3 | ||||
2. Round | 18/08/2019 | Holzwickeder SC | - | SV Schermbeck 1912 | 0:1 | ||||
3. Round | 25/08/2019 | Westfalia Herne | - | Holzwickeder SC | 2:2 | ||||
4. Round | 01/09/2019 | Holzwickeder SC | - | SC Paderborn 07 II | 1:1 | ||||
5. Round | 08/09/2019 | Holzwickeder SC | - | Preußen Münster II | 0:2 | ||||
6. Round | 15/09/2019 | FCE Rheine | - | Holzwickeder SC | 2:4 | ||||
13. Round | 03/11/2019 | Holzwickeder SC | - | TSG Sprockhövel | 2:1 | ||||
14. Round | 10/11/2019 | RSV Meinerzhagen | - | Holzwickeder SC | 5:0 | ||||
15. Round | 17/11/2019 | Holzwickeder SC | - | TuS Erndtebrück | 7:1 | ||||
16. Round | 01/12/2019 | Rot Weiss Ahlen | - | Holzwickeder SC | 1:2 | ||||
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 |