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| U | UD Oliveirense | - | Gil Vicente | 0:1 | ||
| R | Gil Vicente | - | UD Oliveirense | 0:0 | ||
| U: 01.08.2009 18:00 | R: 08.08.2009 18:00 | Winnaars: Gil Vicente | ||||
| U | Portimonense SC | - | CD Feirense | 1:1 | ||
| R | CD Feirense | - | Portimonense SC | 5:6 d.p. | ||
| U: 01.08.2009 18:00 | R: 09.08.2009 18:00 | Winnaars: Portimonense SC | ||||
| U | AD Carregado | - | Sporting Covilhã | 0:1 | ||
| R | Sporting Covilhã | - | AD Carregado | 1:1 | ||
| U: 02.08.2009 17:00 | R: 09.08.2009 17:00 | Winnaars: Sporting Covilhã | ||||
| U | SC Beira-Mar | - | SC Freamunde | 5:1 | ||
| R | SC Freamunde | - | SC Beira-Mar | 3:0 | ||
| U: 02.08.2009 17:00 | R: 09.08.2009 17:00 | Winnaars: SC Beira-Mar | ||||
| U | CD Fátima | - | Varzim SC | 2:0 | ||
| R | Varzim SC | - | CD Fátima | 1:0 | ||
| U: 02.08.2009 17:00 | R: 08.08.2009 20:00 | Winnaars: CD Fátima | ||||
| U | GD Chaves | - | CD Santa Clara | 1:0 | ||
| R | CD Santa Clara | - | GD Chaves | 3:2 | ||
| U: 02.08.2009 17:00 | R: 09.08.2009 18:00 | Winnaars: GD Chaves | ||||
| U | FC Penafiel | - | CD Trofense | 2:0 | ||
| R | CD Trofense | - | FC Penafiel | 3:2 d.p. | ||
| U: 02.08.2009 17:00 | R: 09.08.2009 17:00 | Winnaars: CD Trofense | ||||
| U | CD Aves | - | GD Estoril | 1:1 | ||
| R | GD Estoril | - | CD Aves | 1:0 | ||
| U: 02.08.2009 18:00 | R: 08.08.2009 17:00 | Winnaars: GD Estoril | ||||
