1. Round | 18/08/2019 | The New Saints | - | Caernarfon Town | 1:0 | ||||
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 | ||||
7. Round | 20/09/2019 | Aberystwyth Town | - | Caernarfon Town | 2:3 |