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| 1st(1st leg) | Sporting Covilhã | - | Boavista | dnp | ||
| 2nd (2nd leg) | Boavista | - | Sporting Covilhã | dnp | ||
| 1st(1st leg): 02/08/2008 | 2nd (2nd leg): 10/08/2008 | Winner: Sporting Covilhã | ||||
| 1st(1st leg) | UD Oliveirense | - | GD Estoril | 0:1 | ||
| 2nd (2nd leg) | GD Estoril | - | UD Oliveirense | 1:1 | ||
| 1st(1st leg): 02/08/2008 17:00 | 2nd (2nd leg): 10/08/2008 16:00 | Winner: GD Estoril | ||||
| 1st(1st leg) | Portimonense SC | - | Gil Vicente | 0:2 | ||
| 2nd (2nd leg) | Gil Vicente | - | Portimonense SC | 2:1 | ||
| 1st(1st leg): 02/08/2008 17:00 | 2nd (2nd leg): 09/08/2008 17:00 | Winner: Gil Vicente | ||||
| 1st(1st leg) | CD Feirense | - | FC Vizela | 1:2 | ||
| 2nd (2nd leg) | FC Vizela | - | CD Feirense | 0:0 | ||
| 1st(1st leg): 02/08/2008 17:30 | 2nd (2nd leg): 09/08/2008 17:00 | Winner: FC Vizela | ||||
| 1st(1st leg) | Gondomar SC | - | SC Beira-Mar | 3:1 | ||
| 2nd (2nd leg) | SC Beira-Mar | - | Gondomar SC | 4:5 pso | ||
| 1st(1st leg): 02/08/2008 17:30 | 2nd (2nd leg): 10/08/2008 16:00 | Winner: Gondomar SC | ||||
| 1st(1st leg) | Varzim SC | - | União Leiria | 0:0 | ||
| 2nd (2nd leg) | União Leiria | - | Varzim SC | 1:0 | ||
| 1st(1st leg): 02/08/2008 18:00 | 2nd (2nd leg): 09/08/2008 18:00 | Winner: União Leiria | ||||
| 1st(1st leg) | CD Santa Clara | - | SC Olhanense | 0:0 | ||
| 2nd (2nd leg) | SC Olhanense | - | CD Santa Clara | 2:1 | ||
| 1st(1st leg): 02/08/2008 19:00 | 2nd (2nd leg): 10/08/2008 17:30 | Winner: SC Olhanense | ||||
| 1st(1st leg) | SC Freamunde | - | CD Aves | 3:1 | ||
| 2nd (2nd leg) | CD Aves | - | SC Freamunde | 2:4 pso | ||
| 1st(1st leg): 02/08/2008 20:30 | 2nd (2nd leg): 10/08/2008 19:45 | Winner: SC Freamunde | ||||
