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| 1st(1st leg) | UD Oliveirense | - | Gil Vicente | 0:1 | ||
| 2nd (2nd leg) | Gil Vicente | - | UD Oliveirense | 0:0 | ||
| 1st(1st leg): 01/08/2009 17:00 | 2nd (2nd leg): 08/08/2009 17:00 | Winner: Gil Vicente | ||||
| 1st(1st leg) | Portimonense SC | - | CD Feirense | 1:1 | ||
| 2nd (2nd leg) | CD Feirense | - | Portimonense SC | 5:6 pso | ||
| 1st(1st leg): 01/08/2009 17:00 | 2nd (2nd leg): 09/08/2009 17:00 | Winner: Portimonense SC | ||||
| 1st(1st leg) | AD Carregado | - | Sporting Covilhã | 0:1 | ||
| 2nd (2nd leg) | Sporting Covilhã | - | AD Carregado | 1:1 | ||
| 1st(1st leg): 02/08/2009 16:00 | 2nd (2nd leg): 09/08/2009 16:00 | Winner: Sporting Covilhã | ||||
| 1st(1st leg) | SC Beira-Mar | - | SC Freamunde | 5:1 | ||
| 2nd (2nd leg) | SC Freamunde | - | SC Beira-Mar | 3:0 | ||
| 1st(1st leg): 02/08/2009 16:00 | 2nd (2nd leg): 09/08/2009 16:00 | Winner: SC Beira-Mar | ||||
| 1st(1st leg) | CD Fátima | - | Varzim SC | 2:0 | ||
| 2nd (2nd leg) | Varzim SC | - | CD Fátima | 1:0 | ||
| 1st(1st leg): 02/08/2009 16:00 | 2nd (2nd leg): 08/08/2009 19:00 | Winner: CD Fátima | ||||
| 1st(1st leg) | GD Chaves | - | CD Santa Clara | 1:0 | ||
| 2nd (2nd leg) | CD Santa Clara | - | GD Chaves | 3:2 | ||
| 1st(1st leg): 02/08/2009 16:00 | 2nd (2nd leg): 09/08/2009 17:00 | Winner: GD Chaves | ||||
| 1st(1st leg) | FC Penafiel | - | CD Trofense | 2:0 | ||
| 2nd (2nd leg) | CD Trofense | - | FC Penafiel | 3:2 pso | ||
| 1st(1st leg): 02/08/2009 16:00 | 2nd (2nd leg): 09/08/2009 16:00 | Winner: CD Trofense | ||||
| 1st(1st leg) | CD Aves | - | GD Estoril | 1:1 | ||
| 2nd (2nd leg) | GD Estoril | - | CD Aves | 1:0 | ||
| 1st(1st leg): 02/08/2009 17:00 | 2nd (2nd leg): 08/08/2009 16:00 | Winner: GD Estoril | ||||
