| 1. Round | 16/08/2008 | GAP Connah's Quay FC | - | Haverfordwest County | 2:1 |  |
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| 2. Round | 22/08/2008 | Haverfordwest County | - | Carmarthen Town | 1:1 | |
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| 4. Round | 05/09/2008 | Haverfordwest County | - | Caersws FC | 2:0 | |
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| 6. Round | 20/09/2008 | Haverfordwest County | - | Airbus UK | 3:0 | |
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| 7. Round | 27/09/2008 | Technogroup Welshpool Town | - | Haverfordwest County | 1:3 | |
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| 8. Round | 10/10/2008 | Haverfordwest County | - | The New Saints | 2:2 | |
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| 12. Round | 15/11/2008 | Haverfordwest County | - | Caernarfon Town | 1:1 | |
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| 14. Round | 29/11/2008 | Haverfordwest County | - | Porthmadog FC | 4:2 | |
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| 17. Round | 20/12/2008 | Haverfordwest County | - | GAP Connah's Quay FC | 2:0 | |
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| 18. Round | 27/12/2008 | Haverfordwest County | - | Aberystwyth Town | 5:1 | |
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| 23. Round | 24/01/2009 | Haverfordwest County | - | Rhyl FC | 1:3 | |
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| 24. Round | 07/02/2009 | Airbus UK | - | Haverfordwest County | 2:4 | |
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| 25. Round | 14/02/2009 | Haverfordwest County | - | Technogroup Welshpool Town | 3:1 | |
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| 29. Round | 21/03/2009 | Haverfordwest County | - | Newtown AFC | 1:0 | |
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| 34. Round | 25/04/2009 | Haverfordwest County | - | Neath FC | 2:0 | |
Wales