| 1. Round | 15/08/2008 | NEWI Cefn Druids | - | Technogroup Welshpool Town | 3:3 |  |
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| 4. Round | 05/09/2008 | Caernarfon Town | - | Technogroup Welshpool Town | 2:3 | |
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| 5. Round | 14/09/2008 | Technogroup Welshpool Town | - | Llanelli AFC | 1:3 | |
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| 6. Round | 20/09/2008 | Porthmadog FC | - | Technogroup Welshpool Town | 2:1 | |
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| 8. Round | 12/10/2008 | Neath FC | - | Technogroup Welshpool Town | 3:2 | |
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| 17. Round | 19/12/2008 | Technogroup Welshpool Town | - | NEWI Cefn Druids | 3:3 | |
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| 21. Round | 27/01/2009 | Technogroup Welshpool Town | - | Newtown AFC | 2:2 | |
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| 20. Round | 17/02/2009 | Technogroup Welshpool Town | - | Prestatyn Town | 2:2 | |
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| 31. Round | 03/04/2009 | Caersws FC | - | Technogroup Welshpool Town | 0:1 | |
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| 19. Round | 13/04/2009 | Technogroup Welshpool Town | - | The New Saints | 1:2 | |
Wales