| 1. Round | 16/08/2019 | Penybont FC | - | Barry Town United | 1:2 |  |
|||
| 14. Round | 09/11/2019 | Barry Town United | - | Connah's Quay Nomads | 0:4 | ||||
| 15. Round | 16/11/2019 | Cefn Druids | - | Barry Town United | 1:0 | ||||
| 16. Round | 30/11/2019 | Barry Town United | - | Newtown AFC | 0:1 | ||||
| 17. Round | 13/12/2019 | Barry Town United | - | The New Saints | 1:4 | ||||
| 18. Round | 20/12/2019 | Aberystwyth Town | - | Barry Town United | 0:1 |  |
|||
| 19. Round | 26/12/2019 | Barry Town United | - | Cardiff Metropolitan | 1:1 |  |
Wales