| 1. Round | 11/08/2019 | Rot Weiss Ahlen | - | FCE Rheine | 2:0 |  |
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| 2. Round | 18/08/2019 | TuS Ennepetal | - | Rot Weiss Ahlen | 1:0 | ||||
| 3. Round | 25/08/2019 | Rot Weiss Ahlen | - | Westfalia Rhynern | 2:1 | ||||
| 4. Round | 01/09/2019 | 1. FC Kaan-Marienborn | - | Rot Weiss Ahlen | 1:3 | ||||
| 5. Round | 06/09/2019 | Rot Weiss Ahlen | - | SC Wiedenbrück | 1:1 | |
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| 6. Round | 15/09/2019 | ASC 09 Dortmund | - | Rot Weiss Ahlen | 0:2 | |
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| 7. Round | 20/09/2019 | Rot Weiss Ahlen | - | FC Gütersloh | 1:1 | ||||
| 8. Round | 29/09/2019 | TSG Sprockhövel | - | Rot Weiss Ahlen | 2:1 | |
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| 9. Round | 06/10/2019 | Rot Weiss Ahlen | - | RSV Meinerzhagen | 0:0 | ||||
| 10. Round | 13/10/2019 | TuS Erndtebrück | - | Rot Weiss Ahlen | 1:4 | ||||
| 11. Round | 20/10/2019 | SC Paderborn 07 II | - | Rot Weiss Ahlen | 1:2 | ||||
| 12. Round | 27/10/2019 | Rot Weiss Ahlen | - | Hammer SpVg | 3:1 | |
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| 14. Round | 10/11/2019 | Rot Weiss Ahlen | - | SV Schermbeck 1912 | 3:1 | ||||
| 15. Round | 17/11/2019 | Westfalia Herne | - | Rot Weiss Ahlen | 0:1 | ||||
| 16. Round | 01/12/2019 | Rot Weiss Ahlen | - | Holzwickeder SC | 1:2 | ||||
| 21. Round | 01/03/2020 | Rot Weiss Ahlen | - | 1. FC Kaan-Marienborn | 0:3 | |
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| 22. Round | 06/03/2020 | SC Wiedenbrück | - | Rot Weiss Ahlen | 0:1 |
Germany