| 1. Round | 16/08/2019 | Newtown AFC | - | Cefn Druids | 0:0 | ||||
| 2. Round | 23/08/2019 | Carmarthen Town | - | Newtown AFC | 1:2 | ||||
| 4. Round | 30/08/2019 | Cardiff Metropolitan | - | Newtown AFC | 1:0 | ||||
| 5. Round | 10/09/2019 | The New Saints | - | Newtown AFC | 2:1 |  |
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| 6. Round | 14/09/2019 | Newtown AFC | - | Bala Town | 1:0 |  |
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| 7. Round | 20/09/2019 | Newtown AFC | - | Connah's Quay Nomads | 1:1 | ||||
| 8. Round | 27/09/2019 | Caernarfon Town | - | Newtown AFC | 1:0 | ||||
| 9. Round | 05/10/2019 | Newtown AFC | - | Barry Town United | 2:3 | ||||
| 10. Round | 11/10/2019 | Cefn Druids | - | Newtown AFC | 1:2 | ||||
| 11. Round | 19/10/2019 | Airbus UK | - | Newtown AFC | 2:0 | ||||
| 12. Round | 25/10/2019 | Newtown AFC | - | Cardiff Metropolitan | 1:0 | ||||
| 13. Round | 01/11/2019 | Bala Town | - | Newtown AFC | 4:0 |  |
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| 17. Round | 14/12/2019 | Newtown AFC | - | Carmarthen Town | 1:0 | ||||
| 18. Round | 21/12/2019 | Penybont FC | - | Newtown AFC | 0:2 | ||||
| 19. Round | 26/12/2019 | Newtown AFC | - | Aberystwyth Town | 0:0 | ||||
| 20. Round | 30/12/2019 | Aberystwyth Town | - | Newtown AFC | 1:2 | |
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| 21. Round | 10/01/2020 | Newtown AFC | - | The New Saints | 0:2 | ||||
| 22. Round | 18/01/2020 | Newtown AFC | - | Airbus UK | 0:0 |
England