Friday, October 2, 2009
Académica de Coimbra 2 - 4 Maritimo

Saturday, October 3, 2009
Naval 1º Maio 3 - 2 Rio Ave
Braga 2 - 0 Vitoria Setubal

Sunday, October 4, 2009
Leixoes 3 - 2 Uniao de Leiria
Sporting Lisbon 0 - 0 Belenenses
Olhanense 0 - 3 FC Porto

Monday, October 5, 2009
CD Nacional de Madeira 2 - 0 Guimaraes
Paços de Ferreira 1 - 3 Benfica

Monday, October 12, 2009
Belenenses 0 - 1 CD Nacional de Madeira

Friday, October 23, 2009
Belenenses 0 - 0 Olhanense

Saturday, October 24, 2009
Uniao de Leiria 2 - 0 Naval 1º Maio
Rio Ave 1 - 1 Braga

Sunday, October 25, 2009
Maritimo 3 - 1 Paços de Ferreira
Vitoria Setubal 1 - 0 Leixoes
FC Porto 3 - 2 Académica de Coimbra

Monday, October 26, 2009
Benfica 6 - 1 CD Nacional de Madeira

Tuesday, October 27, 2009
Guimaraes 1 - 1 Sporting Lisbon

Friday, October 30, 2009
FC Porto 1 - 1 Belenenses

Saturday, October 31, 2009
Naval 1º Maio 1 - 0 Leixoes
Braga 2 - 0 Benfica