| 2. Round | 23/08/2019 | Caernarfon Town | - | Connah's Quay Nomads | 0:0 | ||||
| 3. Round | 26/08/2019 | Caernarfon Town | - | Cefn Druids | 1:1 | ||||
| 4. Round | 30/08/2019 | Airbus UK | - | Caernarfon Town | 2:3 | ||||
| 6. Round | 14/09/2019 | Caernarfon Town | - | Penybont FC | 3:2 | ||||
| 8. Round | 27/09/2019 | Caernarfon Town | - | Newtown AFC | 1:0 | ||||
| 9. Round | 04/10/2019 | Caernarfon Town | - | The New Saints | 1:0 | ||||
| 10. Round | 15/10/2019 | Connah's Quay Nomads | - | Caernarfon Town | 4:2 | ||||
| 11. Round | 18/10/2019 | Cefn Druids | - | Caernarfon Town | 3:1 | ||||
| 13. Round | 02/11/2019 | Caernarfon Town | - | Barry Town United | 4:1 | ||||
| 14. Round | 08/11/2019 | Newtown AFC | - | Caernarfon Town | 3:1 | ||||
| 17. Round | 13/12/2019 | Caernarfon Town | - | Airbus UK | 5:0 |  |
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| 19. Round | 26/12/2019 | Caernarfon Town | - | Bala Town | 1:2 | ||||
| 15. Round | 04/01/2020 | Penybont FC | - | Caernarfon Town | 0:0 | ||||
| 21. Round | 10/01/2020 | Caernarfon Town | - | Aberystwyth Town | 0:3 | ||||
| 22. Round | 18/01/2020 | Cardiff Metropolitan | - | Caernarfon Town | 2:0 |
Wales