| 2. Round | 23/08/2008 | Prestatyn Town | - | Technogroup Welshpool Town | 2:2 |  |
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| 12. Round | 15/11/2008 | Bangor City | - | Technogroup Welshpool Town | 0:2 | |
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| 13. Round | 21/11/2008 | Technogroup Welshpool Town | - | Caersws FC | 1:0 | |
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| 15. Round | 05/12/2008 | Technogroup Welshpool Town | - | Airbus UK | 2:1 | |
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| 18. Round | 26/12/2008 | The New Saints | - | Technogroup Welshpool Town | 3:1 | |
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| 22. Round | 16/01/2009 | Technogroup Welshpool Town | - | Caernarfon Town | 1:1 | |
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| 27. Round | 06/03/2009 | Aberystwyth Town | - | Technogroup Welshpool Town | 0:2 | |
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| 16. Round | 10/03/2009 | Technogroup Welshpool Town | - | Port Talbot Town | 1:2 | |
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| 28. Round | 13/03/2009 | Technogroup Welshpool Town | - | GAP Connah's Quay FC | 3:1 | |
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| 24. Round | 17/03/2009 | Technogroup Welshpool Town | - | Porthmadog FC | 3:2 | |
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| 30. Round | 27/03/2009 | Technogroup Welshpool Town | - | Bangor City | 1:1 | |
England