| 4. Round | 01/09/2019 | Holzwickeder SC | - | SC Paderborn 07 II | 1:1 |  |
|||
| 6. Round | 15/09/2019 | Preußen Münster II | - | SC Paderborn 07 II | 3:2 | ||||
| 7. Round | 22/09/2019 | SC Paderborn 07 II | - | RSV Meinerzhagen | 4:1 | |
|||
| 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 | |
USA