AD Carregado 1-2 SC Covilha *
| 09.08.2009 | SC Covilha | 1-1 | AD Carregado | |
| 02.08.2009 | AD Carregado | 0-1 | SC Covilha | |
CD Aves 1-2 GD Estoril *
| 08.08.2009 | GD Estoril | 1-0 | CD Aves | |
| 02.08.2009 | CD Aves | 1-1 | GD Estoril | |
FC Penafiel 2-2 CD Trofense *
| 09.08.2009 | CD Trofense | 2-0/p.3-2 | FC Penafiel | |
| 02.08.2009 | FC Penafiel | 2-0 | CD Trofense | |
GD Chaves 3-3 CD Santa Clara *
| 09.08.2009 | CD Santa Clara | 3-2/p.4-2 | GD Chaves | |
| 02.08.2009 | GD Chaves | 1-0 | CD Santa Clara | |
*Portimonense SC 1-1 CD Feirense
| 09.08.2009 | CD Feirense | 0-0/p.5-6 | Portimonense SC | |
| 01.08.2009 | Portimonense SC | 1-1 | CD Feirense | |
*SC Beira-Mar 5-4 SC Freamunde
| 09.08.2009 | SC Freamunde | 3-0 | SC Beira-Mar | |
| 02.08.2009 | SC Beira-Mar | 5-1 | SC Freamunde | |
UD Oliveirense 0-1 Gil Vicente *
| 08.08.2009 | Gil Vicente | 0-0 | UD Oliveirense | |
| 01.08.2009 | UD Oliveirense | 0-1 | Gil Vicente | |