| 1. Round | 16/08/2019 | Penybont FC | - | Barry Town United | 1:2 | ||||
| 2. Round | 23/08/2019 | Penybont FC | - | Cardiff Metropolitan | 1:3 | ||||
| 3. Round | 26/08/2019 | Newtown AFC | - | Penybont FC | 1:1 |  |
 |
||
| 6. Round | 14/09/2019 | Caernarfon Town | - | Penybont FC | 3:2 | ||||
| 7. Round | 21/09/2019 | Penybont FC | - | Airbus UK | 3:1 | |
|
||
| 8. Round | 29/09/2019 | Connah's Quay Nomads | - | Penybont FC | 3:1 | |
|||
| 9. Round | 04/10/2019 | Penybont FC | - | Aberystwyth Town | 1:1 | ||||
| 11. Round | 19/10/2019 | Penybont FC | - | The New Saints | 2:3 | |
|
||
| 12. Round | 27/10/2019 | Penybont FC | - | Cefn Druids | 2:3 | |
|||
| 13. Round | 01/11/2019 | Cardiff Metropolitan | - | Penybont FC | 1:1 | |
|||
| 10. Round | 22/11/2019 | Barry Town United | - | Penybont FC | 3:0 | ||||
| 16. Round | 30/11/2019 | Penybont FC | - | Connah's Quay Nomads | 0:0 | |
|||
| 17. Round | 17/12/2019 | Bala Town | - | Penybont FC | 4:0 | ||||
| 18. Round | 21/12/2019 | Penybont FC | - | Newtown AFC | 0:2 | |
|||
| 20. Round | 01/01/2020 | Penybont FC | - | Carmarthen Town | 1:1 | |
|||
| 15. Round | 04/01/2020 | Penybont FC | - | Caernarfon Town | 0:0 | ||||
| 21. Round | 11/01/2020 | Cefn Druids | - | Penybont FC | 2:3 | |
|
||
| 22. Round | 18/01/2020 | Aberystwyth Town | - | Penybont FC | 1:0 |
Wales