| 1. Round | 09/08/2019 | FC Gütersloh | - | SC Wiedenbrück | 1:1 | ||||
| 2. Round | 18/08/2019 | SC Wiedenbrück | - | TSG Sprockhövel | 5:2 | ||||
| 3. Round | 25/08/2019 | RSV Meinerzhagen | - | SC Wiedenbrück | 5:0 | ||||
| 4. Round | 01/09/2019 | SC Wiedenbrück | - | TuS Erndtebrück | 2:1 | ||||
| 5. Round | 06/09/2019 | Rot Weiss Ahlen | - | SC Wiedenbrück | 1:1 | ||||
| 7. Round | 22/09/2019 | Sportfreunde Siegen | - | SC Wiedenbrück | 0:2 | ||||
| 8. Round | 29/09/2019 | SC Wiedenbrück | - | SV Schermbeck 1912 | 3:0 | ||||
| 9. Round | 06/10/2019 | Westfalia Herne | - | SC Wiedenbrück | 0:3 |  |
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| 11. Round | 20/10/2019 | Preußen Münster II | - | SC Wiedenbrück | 0:1 | ||||
| 12. Round | 25/10/2019 | SC Wiedenbrück | - | FCE Rheine | 0:0 | ||||
| 13. Round | 03/11/2019 | TuS Ennepetal | - | SC Wiedenbrück | 0:3 | ||||
| 14. Round | 08/11/2019 | SC Wiedenbrück | - | Westfalia Rhynern | 3:2 | ||||
| 15. Round | 17/11/2019 | 1. FC Kaan-Marienborn | - | SC Wiedenbrück | 1:2 | ||||
| 17. Round | 08/12/2019 | SC Wiedenbrück | - | ASC 09 Dortmund | 1:0 |
Germany