| 2. Round | 23/08/2019 | Caernarfon Town | - | Connah's Quay Nomads | 0:0 |  |
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| 5. Round | 07/09/2019 | Barry Town United | - | Caernarfon Town | 0:0 | ||||
| 6. Round | 14/09/2019 | Caernarfon Town | - | Penybont FC | 3:2 | ||||
| 7. Round | 20/09/2019 | Aberystwyth Town | - | Caernarfon Town | 2:3 | ||||
| 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 | |
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| 12. Round | 26/10/2019 | Caernarfon Town | - | Carmarthen Town | 2:0 | ||||
| 13. Round | 02/11/2019 | Caernarfon Town | - | Barry Town United | 4:1 | ||||
| 14. Round | 08/11/2019 | Newtown AFC | - | Caernarfon Town | 3:1 | ||||
| 16. Round | 29/11/2019 | Caernarfon Town | - | Cardiff Metropolitan | 2:1 | ||||
| 17. Round | 13/12/2019 | Caernarfon Town | - | Airbus UK | 5:0 | ||||
| 18. Round | 21/12/2019 | Carmarthen Town | - | Caernarfon Town | 0:1 |  |
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| 20. Round | 30/12/2019 | Bala Town | - | Caernarfon Town | 3:0 | ||||
| 15. Round | 04/01/2020 | Penybont FC | - | Caernarfon Town | 0:0 |
Wales