| 2. Round | 18/08/2019 | Westfalia Herne | - | SC Paderborn 07 II | 0:1 | ||||
| 3. Round | 25/08/2019 | SC Paderborn 07 II | - | FC Gütersloh | 5:3 |  |
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| 10. Round | 13/10/2019 | TuS Ennepetal | - | SC Paderborn 07 II | 3:1 | ||||
| 11. Round | 20/10/2019 | SC Paderborn 07 II | - | Rot Weiss Ahlen | 1:2 | |
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| 12. Round | 25/10/2019 | Westfalia Rhynern | - | SC Paderborn 07 II | 4:0 | |
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| 13. Round | 03/11/2019 | SC Paderborn 07 II | - | Hammer SpVg | 4:2 | |
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| 14. Round | 10/11/2019 | 1. FC Kaan-Marienborn | - | SC Paderborn 07 II | 4:0 | ||||
| 15. Round | 17/11/2019 | SC Paderborn 07 II | - | Sportfreunde Siegen | 1:1 | |
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| 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 | ||||
| 21. Round | 01/03/2020 | SC Paderborn 07 II | - | Holzwickeder SC | 3:2 | |
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Germany