| 1. Round | 18/08/2019 | The New Saints | - | Caernarfon Town | 1:0 |  |
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| 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 | ||||
| 5. Round | 07/09/2019 | Barry Town United | - | Caernarfon Town | 0:0 | |
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| 6. Round | 14/09/2019 | Caernarfon Town | - | Penybont FC | 3:2 |  |
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| 7. Round | 20/09/2019 | Aberystwyth Town | - | Caernarfon Town | 2:3 | ||||
| 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 | |
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| 12. Round | 26/10/2019 | Caernarfon Town | - | Carmarthen Town | 2:0 | ||||
| 22. Round | 18/01/2020 | Cardiff Metropolitan | - | Caernarfon Town | 2:0 |
Wales