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| H | Neath FC | - | The New Saints | 2:0 | ||
| R | The New Saints | - | Neath FC | 3:0 | ||
| H: 25.11.2008 20:30 | R: 09.12.2008 20:30 | Sieger: The New Saints | ||||
| H | Bangor City | - | Aberystwyth Town | 1:2 | ||
| R | Aberystwyth Town | - | Bangor City | 2:4 | ||
| H: 09.12.2008 20:30 | R: 13.01.2009 20:30 | Sieger: Bangor City | ||||
