| 3. Round | 26/08/2019 | Aberystwyth Town | - | The New Saints | 1:10 | ||||
| 4. Round | 31/08/2019 | The New Saints | - | Penybont FC | 2:1 | ||||
| 5. Round | 10/09/2019 | The New Saints | - | Newtown AFC | 2:1 | ||||
| 6. Round | 16/09/2019 | Cardiff Metropolitan | - | The New Saints | 1:1 |  |
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| 8. Round | 28/09/2019 | The New Saints | - | Barry Town United | 0:1 | ||||
| 9. Round | 04/10/2019 | Caernarfon Town | - | The New Saints | 1:0 | ||||
| 10. Round | 12/10/2019 | The New Saints | - | Airbus UK | 6:2 | ||||
| 12. Round | 25/10/2019 | The New Saints | - | Bala Town | 1:0 |  |
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| 13. Round | 01/11/2019 | Connah's Quay Nomads | - | The New Saints | 1:1 | |
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| 15. Round | 15/11/2019 | The New Saints | - | Aberystwyth Town | 2:0 | |
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| 16. Round | 30/11/2019 | Airbus UK | - | The New Saints | 0:12 | ||||
| 14. Round | 03/12/2019 | The New Saints | - | Carmarthen Town | 1:0 | ||||
| 17. Round | 13/12/2019 | Barry Town United | - | The New Saints | 1:4 | |
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| 18. Round | 20/12/2019 | The New Saints | - | Cardiff Metropolitan | 1:2 | |
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| 19. Round | 26/12/2019 | Cefn Druids | - | The New Saints | 0:5 | ||||
| 20. Round | 30/12/2019 | The New Saints | - | Cefn Druids | 2:1 | ||||
| 21. Round | 10/01/2020 | Newtown AFC | - | The New Saints | 0:2 | |
Wales