| 2. Round | 19/08/2019 | CD Tondela | - | Portimonense SC | 1:2 | ||||
| 3. Round | 25/08/2019 | Portimonense SC | - | Sporting CP | 1:3 | ||||
| 4. Round | 30/08/2019 | Moreirense FC | - | Portimonense SC | 1:0 | ||||
| 5. Round | 15/09/2019 | Portimonense SC | - | FC Porto | 2:3 | ||||
| 7. Round | 29/09/2019 | Portimonense SC | - | Sporting Braga | 0:1 | ||||
| 10. Round | 04/11/2019 | Portimonense SC | - | CD Santa Clara | 1:1 | ||||
| 15. Round | 04/01/2020 | Boavista | - | Portimonense SC | 1:1 |
Ecuador