CD Feirense 1-2 FC Vizela
| 09.08.2008 | FC Vizela | 0-0 | CD Feirense | |
| 02.08.2008 | CD Feirense | 1-2 | FC Vizela | |
CD Santa Clara 1-2 SC Olhanense
| 10.08.2008 | SC Olhanense | 2-1 | CD Santa Clara | |
| 02.08.2008 | CD Santa Clara | 0-0 | SC Olhanense | |
Portimonense SC 1-4 Gil Vicente
| 09.08.2008 | Gil Vicente | 2-1 | Portimonense SC | |
| 02.08.2008 | Portimonense SC | 0-2 | Gil Vicente | |
Gondomar SC 3-3 SC Beira-Mar
| 10.08.2008 | SC Beira-Mar | 2-0/p.4-5 | Gondomar SC | |
| 02.08.2008 | Gondomar SC | 3-1 | SC Beira-Mar | |
*SC Freamunde 3-3 CD Aves
| 10.08.2008 | CD Aves | 2-0/p.2-4 | SC Freamunde | |
| 02.08.2008 | SC Freamunde | 3-1 | CD Aves | |
UD Oliveirense 1-2 GD Estoril
| 10.08.2008 | UD Oliveirense | 1-1 | GD Estoril | |
| 02.08.2008 | UD Oliveirense | 0-1 | GD Estoril | |
Varzim SC 0-1 Uniao Leiria
| 09.08.2008 | Uniao Leiria | 1-0 | Varzim SC | |
| 02.08.2008 | Varzim SC | 0-0 | Uniao Leiria | |