| 1. Round | 11/08/2019 | SC Paderborn 07 II | - | ASC 09 Dortmund | 1:2 |  |
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| 2. Round | 18/08/2019 | Westfalia Herne | - | SC Paderborn 07 II | 0:1 | ||||
| 6. Round | 15/09/2019 | Preußen Münster II | - | SC Paderborn 07 II | 3:2 | |
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| 7. Round | 22/09/2019 | SC Paderborn 07 II | - | RSV Meinerzhagen | 4:1 | ||||
| 8. Round | 29/09/2019 | FCE Rheine | - | SC Paderborn 07 II | 2:3 | ||||
| 13. Round | 03/11/2019 | SC Paderborn 07 II | - | Hammer SpVg | 4:2 | ||||
| 14. Round | 10/11/2019 | 1. FC Kaan-Marienborn | - | SC Paderborn 07 II | 4:0 | ||||
| 16. Round | 01/12/2019 | SC Paderborn 07 II | - | SC Wiedenbrück | 5:0 | ||||
| 17. Round | 08/12/2019 | SV Schermbeck 1912 | - | SC Paderborn 07 II | 2:1 | ||||
| 18. Round | 15/12/2019 | ASC 09 Dortmund | - | SC Paderborn 07 II | 1:2 | ||||
| 19. Round | 08/02/2020 | SC Paderborn 07 II | - | Westfalia Herne | 1:1 | ||||
| 20. Round | 14/02/2020 | FC Gütersloh | - | SC Paderborn 07 II | 1:1 |  |
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| 21. Round | 01/03/2020 | SC Paderborn 07 II | - | Holzwickeder SC | 3:2 |  |
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| 22. Round | 08/03/2020 | TSG Sprockhövel | - | SC Paderborn 07 II | 0:1 |
Germany