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| 1st(1st leg) | Neath FC | - | The New Saints | 2:0 | ||
| 2nd (2nd leg) | The New Saints | - | Neath FC | 3:0 | ||
| 1st(1st leg): 25/11/2008 19:30 | 2nd (2nd leg): 09/12/2008 19:30 | Winner: The New Saints | ||||
| 1st(1st leg) | Bangor City | - | Aberystwyth Town | 1:2 | ||
| 2nd (2nd leg) | Aberystwyth Town | - | Bangor City | 2:4 | ||
| 1st(1st leg): 09/12/2008 19:30 | 2nd (2nd leg): 13/01/2009 19:30 | Winner: Bangor City | ||||
