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| H (Match allé) | Neath FC | - | The New Saints | 2:0 | ||
| R (match retour) | The New Saints | - | Neath FC | 3:0 | ||
| H (Match allé): 25.11.2008 20:30 | R (match retour): 09.12.2008 20:30 | vainqueur: The New Saints | ||||
| H (Match allé) | Bangor City | - | Aberystwyth Town | 1:2 | ||
| R (match retour) | Aberystwyth Town | - | Bangor City | 2:4 | ||
| H (Match allé): 09.12.2008 20:30 | R (match retour): 13.01.2009 20:30 | vainqueur: Bangor City | ||||
