| 1. Round | 15/08/2008 | Prestatyn Town | - | Airbus UK | 2:1 |  |
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| 2. Round | 23/08/2008 | Prestatyn Town | - | Technogroup Welshpool Town | 2:2 | |
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| 6. Round | 20/09/2008 | Newtown AFC | - | Prestatyn Town | 1:1 | |
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| 8. Round | 12/10/2008 | Llanelli AFC | - | Prestatyn Town | 6:1 | |
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| 15. Round | 06/12/2008 | Prestatyn Town | - | Bangor City | 2:2 | |
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| 18. Round | 27/12/2008 | Rhyl FC | - | Prestatyn Town | 7:2 | |
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| 20. Round | 17/02/2009 | Technogroup Welshpool Town | - | Prestatyn Town | 2:2 | |
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| 16. Round | 24/03/2009 | Caersws FC | - | Prestatyn Town | 1:2 | |
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| 30. Round | 29/03/2009 | Prestatyn Town | - | Aberystwyth Town | 1:0 | |
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| 31. Round | 03/04/2009 | GAP Connah's Quay FC | - | Prestatyn Town | 3:1 | |
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| 32. Round | 21/04/2009 | Prestatyn Town | - | Carmarthen Town | 1:2 | |
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| 34. Round | 25/04/2009 | Prestatyn Town | - | Caersws FC | 3:2 | |
Wales