| 1. Round | 02/02/2019 | Caernarfon Town | - | Barry Town United | 2:0 | ||||
| 3. Round | 16/02/2019 | The New Saints | - | Barry Town United | 2:2 |  |
|||
| 4. Round | 23/02/2019 | Barry Town United | - | Connah's Quay Nomads | 1:1 | |
 |
||
| 6. Round | 23/03/2019 | Barry Town United | - | Caernarfon Town | 4:0 | |
|||
| 7. Round | 06/04/2019 | Bala Town | - | Barry Town United | 2:5 | ||||
| 8. Round | 13/04/2019 | Barry Town United | - | The New Saints | 0:4 | |
|||
| 9. Round | 20/04/2019 | Connah's Quay Nomads | - | Barry Town United | 1:1 | |
|||
| 10. Round | 26/04/2019 | Barry Town United | - | Newtown AFC | 1:3 |
Wales