| 3. Round | 30/08/2008 | Caersws FC | - | Porthmadog FC | 3:2 |  |
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| 5. Round | 12/09/2008 | Airbus UK | - | Porthmadog FC | 0:3 | |
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| 6. Round | 20/09/2008 | Porthmadog FC | - | Technogroup Welshpool Town | 2:1 | |
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| 9. Round | 17/10/2008 | Prestatyn Town | - | Porthmadog FC | 5:2 | |
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| 10. Round | 25/10/2008 | Porthmadog FC | - | Newtown AFC | 3:1 | |
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| 11. Round | 07/11/2008 | Caernarfon Town | - | Porthmadog FC | 0:2 | |
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| 12. Round | 15/11/2008 | Porthmadog FC | - | Llanelli AFC | 3:3 | |
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| 13. Round | 22/11/2008 | Port Talbot Town | - | Porthmadog FC | 1:3 | |
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| 18. Round | 27/12/2008 | Porthmadog FC | - | GAP Connah's Quay FC | 6:5 | |
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| 23. Round | 24/01/2009 | Porthmadog FC | - | Airbus UK | 3:4 | |
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| 27. Round | 07/03/2009 | Porthmadog FC | - | Prestatyn Town | 3:2 | |
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| 24. Round | 17/03/2009 | Technogroup Welshpool Town | - | Porthmadog FC | 3:2 | |
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| 29. Round | 21/03/2009 | Porthmadog FC | - | Caernarfon Town | 1:3 | |
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| 32. Round | 11/04/2009 | Porthmadog FC | - | Haverfordwest County | 2:1 | |
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| 19. Round | 13/04/2009 | GAP Connah's Quay FC | - | Porthmadog FC | 3:1 | |
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| 34. Round | 25/04/2009 | Porthmadog FC | - | Aberystwyth Town | 4:1 | |
Wales