| 1. Round | 25/08/2019 | Siegburger SV 04 | - | Spvg Wesseling-Urfeld | 1:2 | ||||
| 2. Round | 01/09/2019 | FC Pesch 1956 | - | Siegburger SV 04 | 4:0 | ||||
| 3. Round | 08/09/2019 | Siegburger SV 04 | - | VfL 08 Vichttal | 0:2 dec. |  |
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| 4. Round | 15/09/2019 | SV Deutz 05 | - | Siegburger SV 04 | 0:1 | ||||
| 5. Round | 22/09/2019 | Fortuna Köln II | - | Siegburger SV 04 | 1:2 | ||||
| 6. Round | 29/09/2019 | Siegburger SV 04 | - | SpVg Frechen 20 | 2:1 | ||||
| 7. Round | 06/10/2019 | Viktoria Arnoldsweiler | - | Siegburger SV 04 | 1:4 | |
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| 8. Round | 13/10/2019 | Siegburger SV 04 | - | Borussia Freialdenhoven | 2:1 | ||||
| 9. Round | 20/10/2019 | FC Hürth | - | Siegburger SV 04 | 0:2 | |
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| 10. Round | 27/10/2019 | Siegburger SV 04 | - | SV Breinig | 3:0 | |
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| 11. Round | 03/11/2019 | SV 1914 Eilendorf | - | Siegburger SV 04 | 0:3 | |
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| 12. Round | 10/11/2019 | Siegburger SV 04 | - | FC Hennef 05 | 0:2 | ||||
| 13. Round | 17/11/2019 | Blau-Weiß Friesdorf | - | Siegburger SV 04 | 3:2 | ||||
| 14. Round | 01/12/2019 | Siegburger SV 04 | - | 1. FC Düren | 0:2 | ||||
| 15. Round | 08/12/2019 | FC Wegberg-Beeck | - | Siegburger SV 04 | 0:0 | ||||
| 16. Round | 01/03/2020 | Spvg Wesseling-Urfeld | - | Siegburger SV 04 | 0:1 |
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