| 1. Round | 16/08/2019 | Penybont FC | - | Barry Town United | 1:2 |  |
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| 4. Round | 30/08/2019 | Carmarthen Town | - | Barry Town United | 0:1 | ||||
| 5. Round | 07/09/2019 | Barry Town United | - | Caernarfon Town | 0:0 | ||||
| 11. Round | 19/10/2019 | Bala Town | - | Barry Town United | 1:1 | ||||
| 12. Round | 26/10/2019 | Barry Town United | - | Airbus UK | 2:0 |  |
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| 13. Round | 02/11/2019 | Caernarfon Town | - | Barry Town United | 4:1 | |
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| 14. Round | 09/11/2019 | Barry Town United | - | Connah's Quay Nomads | 0:4 | |
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| 17. Round | 13/12/2019 | Barry Town United | - | The New Saints | 1:4 | |
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| 18. Round | 20/12/2019 | Aberystwyth Town | - | Barry Town United | 0:1 | |
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| 20. Round | 30/12/2019 | Cardiff Metropolitan | - | Barry Town United | 0:1 |
Wales