| 2. Round | 22/08/2008 | NEWI Cefn Druids | - | The New Saints | 0:1 |  |
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| 5. Round | 12/09/2008 | The New Saints | - | Caernarfon Town | 6:0 | |
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| 7. Round | 27/09/2008 | The New Saints | - | Porthmadog FC | 6:0 | |
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| 14. Round | 29/11/2008 | Caersws FC | - | The New Saints | 2:6 | |
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| 20. Round | 03/01/2009 | The New Saints | - | NEWI Cefn Druids | 4:1 | |
England
