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 | ||||
7. Round | 22/09/2019 | Holzwickeder SC | - | TuS Ennepetal | 3:2 | ||||
8. Round | 29/09/2019 | Westfalia Rhynern | - | Holzwickeder SC | 3:0 | ||||
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 | ||||
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 | ||||
17. Round | 08/12/2019 | Holzwickeder SC | - | Hammer SpVg | 4:2 | ||||
18. Round | 22/02/2020 | Holzwickeder SC | - | Sportfreunde Siegen | 0:0 |