Ronde 1
| 01/08/2009 | 17:00 | Portimonense | 1-1 | Feirense |
|
| 01/08/2009 | 17:00 | Oliveirense | 0-1 | Gil Vicente |
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| 02/08/2009 | 17:00 | Beira Mar | 5-1 | Freamunde |
|
| 02/08/2009 | 17:00 | Fátima | 2-0 | Varzim |
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| 02/08/2009 | 17:00 | Chaves | 1-0 | CD Santa Clara |
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| 02/08/2009 | 18:00 | CD Aves | 1-1 | Estoril |
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Ronde n°1 (R)
| 08/08/2009 | 17:00 | Estoril | 1-0 | CD Aves |
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| 08/08/2009 | 17:00 | Gil Vicente | 0-0 | Oliveirense |
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| 08/08/2009 | 20:00 | Varzim | 1-0 | Fátima |
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| 09/08/2009 | 17:00 | CD Santa Clara | 3-2 | Chaves |
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| 09/08/2009 | 17:00 | Freamunde | 3-0 | Beira Mar |
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| 09/08/2009 | 17:00 | Sporting Covilhã | 1-1 | Carregado |
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| 09/08/2009 | 17:00 | Trofense | P2-0 | Penafiel |
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| 09/08/2009 | 18:00 | Feirense | 0-0P | Portimonense |
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