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Results
Second Round
Portugal - 3 August 2019 - 5 August 2019
Results - - Second Round 2019/2020
3 August 2019 | ||||
| 17h00 | Casa Pia AC | 2 - 0 |  Boavista | |
| 17h00 | CD Nacional Madeira | 2 - 2 (3 pen 4) |  GD Chaves | |
| 17h00 | Leixões SC | 1 - 2 |  Marítimo Funchal | |
| 17h00 | FC Penafiel | 1 - 0 |  CD Tondela | |
| 17h00 | Vitória Setúbal | 1 - 0 |  Moreirense | |
| 18h00 | CF Os Belenenses | 0 - 1 |  Santa Clara Acores SAD | |
| 19h00 | Rio Ave | 6 - 1 |  U.D. Oliveirense | |
| 19h00 | Desportivo das Aves | 2 - 3 |  Gil Vicente | |
| 19h00 | Portimonense SC | 2 - 0 |  Academica Coimbra | |
| 19h00 | FC Paços de Ferreira | 1 - 1 (5 pen 4) |  Estoril-Praia | |
| 19h00 | FC Famalicão | 0 - 2 |  SC Covilhã | |
5 August 2019 | ||||
| 20h45 | CD Feirense | 0 - 1 |  Vitoria SC Guimaraes | |
