| 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 | ||||
| 4. Round | 01/09/2019 | Holzwickeder SC | - | SC Paderborn 07 II | 1:1 | ||||
| 5. Round | 08/09/2019 | SC Paderborn 07 II | - | TSG Sprockhövel | 0:1 | ||||
| 7. Round | 22/09/2019 | SC Paderborn 07 II | - | RSV Meinerzhagen | 4:1 |  |
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| 8. Round | 29/09/2019 | FCE Rheine | - | SC Paderborn 07 II | 2:3 | ||||
| 9. Round | 03/10/2019 | SC Paderborn 07 II | - | TuS Erndtebrück | 2:0 | ||||
| 10. Round | 13/10/2019 | TuS Ennepetal | - | SC Paderborn 07 II | 3:1 | ||||
| 12. Round | 25/10/2019 | Westfalia Rhynern | - | SC Paderborn 07 II | 4:0 | ||||
| 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 | ||||
| 20. Round | 14/02/2020 | FC Gütersloh | - | SC Paderborn 07 II | 1:1 |  |
USA