| | First Leg - 23-03-2010 | | | DATE | | TIME | | HOME | | | | | | AWAY | |  | | | | | | | | | | | 24-03 | 20:15 | Rio Ave | 1 | 3 | FC Porto | | 23-03 | 18:15 | Chaves | 1 | 0 | Naval |
| Second Leg - 13-04-2010 | | | DATE | | TIME | | HOME | | | | | | AWAY | | | | | | | | | | | | | 14-04 | 19:45 | FC Porto | 4 | 0 | Rio Ave | | 13-04 | 18:00 | Naval | 1 | 2 | Chaves |
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| Portuguese Cup | | Quarter-Finals - 02-02-2010 | | | DATE | | TIME | | HOME | | | | | | AWAY | | | | | | | | | | | | | 02-02 | 20:45 | FC Porto | 5 | 2 | Sporting | | 03-02 | 18:15 | Sp. Braga | 5 | 6 | Rio Ave | | 04-02 | 20:15 | Paços Ferreira | 1 | 2 | Chaves | | 03-02 | 14:30 | Pinhalnovense | 1 | 3 | Naval |
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| Portuguese Cup | | Round Of 16 - 19-01-2010 | | | DATE | | TIME | | HOME | | | | | | AWAY | | | | | | | | | | | | | 20-01 | 21:00 | Sporting | 4 | 3 | Mafra | | 20-01 | 19:00 | Rio Ave | 6 | 4 | V. Guimarães | | 20-01 | 16:00 | Nacional | 1 | 2 | Paços Ferreira | | 20-01 | 19:30 | Freamunde | 1 | 3 | Sp. Braga | | 24-01 | 15:00 | Chaves | 1 | 0 | Beira Mar | | 20-01 | 16:00 | Aliados Lordelo | 0 | 1 | Naval | | 20-01 | 15:00 | Camacha | 0 | 1 | Pinhalnovense | | 20-01 | 20:45 | Belenenses | 11 | 12 | FC Porto |
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| Portuguese Cup | | Fourth Round - 22-11-2009 | | | DATE | | TIME | | HOME | | | | | | AWAY | | | | | | | | | | | | | 22-11 | 15:00 | Tirsense | 9 | 10 | Paços Ferreira | | 22-11 | 16:00 | Nacional | 4 | 3 | Fátima | | 22-11 | 15:00 | Rio Ave | 1 | 0 | Santa Clara | | 22-11 | 15:00 | Chaves | 2 | 0 | União Serra | | 22-11 | 16:00 | Naval | 3 | 2 | Gil Vicente | | 22-11 | 15:00 | Aliados Lordelo | 1 | 0 | Leixões | | 22-11 | 19:45 | Benfica | 0 | 1 | V. Guimarães | | 22-11 | 17:45 | Pescadores Costa Caparica | 1 | 4 | Sporting | | 22-11 | 15:00 | Camacha | 1 | 0 | Vigor Mocidade | | 22-11 | 18:00 | Sp. Braga | 3 | 0 | V. Setúbal | | 22-11 | 15:00 | Académica | 4 | 6 | Beira Mar | | 22-11 | 15:00 | Freamunde | 7 | 6 | U. Leiria | | 02-01 | 20:15 | Oliveirense | 0 | 2 | FC Porto | | 22-11 | 15:00 | Oeiras | 1 | 2 | Pinhalnovense | | 22-11 | 14:00 | Valenciano | 0 | 1 | Belenenses | | 22-11 | 14:00 | Mafra | 4 | 3 | U. Madeira |
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| Portuguese Cup | | Third Round - 18-10-2009 | | | DATE | | TIME | | HOME | | | | | | AWAY | | | | | | | | | | | | | 17-10 | 18:15 | Monsanto | 0 | 6 | Benfica | | 18-10 | 18:15 | Sporting | 3 | 0 | Penafiel | | 17-10 | 20:15 | FC Porto | 4 | 0 | Sertanense | | 18-10 | 15:00 | Académica | 2 | 1 | Portimonense | | 18-10 | 15:00 | Paços Ferreira | 3 | 1 | Aljustrelense | | 18-10 | 15:00 | Leixões | 2 | 1 | Casa Pia | | 18-10 | 15:00 | Merelinense | 1 | 2 | U. Leiria | | 18-10 | 16:00 | Santa Clara | 2 | 1 | Marítimo | | 18-10 | 15:00 | Belenenses | 3 | 1 | Oriental | | 18-10 | 16:00 | V. Guimarães | 3 | 1 | Feirense | | 18-10 | 15:00 | Naval | 1 | 0 | Padroense | | 18-10 | 16:00 | Rio Ave | 2 | 1 | Esmoriz | | 17-10 | 18:00 | Varzim | 1 | 2 | Nacional | | 17-10 | 15:00 | Valenciano | 5 | 3 | Olhanense | | 18-10 | 15:00 | Atlético | 0 | 2 | V. Setúbal | | 17-10 | 18:00 | Sp. Covilhã | 0 | 1 | Sp. Braga | | 18-10 | 15:00 | Aliados Lordelo | 2 | 0 | Machico | | 18-10 | 15:00 | Tondela | 0 | 1 | Oliveirense | | 18-10 | 15:00 | Cinfães | 2 | 4 | Pescadores Costa Caparica | | 18-10 | 16:00 | U. Madeira | 2 | 0 | Alcains | | 18-10 | 16:00 | Cruzado Canicense | 1 | 4 | Vigor Mocidade | | 18-10 | 15:00 | Leça | 0 | 3 | Chaves | | 18-10 | 16:00 | Fátima | 3 | 0 | Vila Meã | | 18-10 | 15:00 | Beira Mar | 4 | 0 | Moncorvo | | 18-10 | 15:00 | Oeiras | 6 | 1 | Operário | | 18-10 | 16:00 | Camacha | 3 | 1 | Paredes | | 18-10 | 15:00 | Sintrense | 3 | 4 | Pinhalnovense | | 18-10 | 15:00 | União Serra | 3 | 2 | Coimbrões | | 18-10 | 15:00 | Tirsense | 1 | 0 | Oliv. Bairro | | 18-10 | 15:00 | Freamunde | 3 | 0 | Carregado | | 18-10 | 16:00 | Gil Vicente | 6 | 1 | Nelas | | 04-11 | 14:00 | Vieira | 0 | 1 | Mafra |
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