| 1. Round | 11/08/2019 | SC Paderborn 07 II | - | ASC 09 Dortmund | 1:2 | ||||
| 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 | ||||
| 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 | ||||
| 9. Round | 03/10/2019 | SC Paderborn 07 II | - | TuS Erndtebrück | 2:0 | ||||
| 12. Round | 25/10/2019 | Westfalia Rhynern | - | 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 |  |
Germany