| 1. Round | 19/08/1989 | GD Chaves | - | FC Penafiel | 3:2 | ||||
| 4. Round | 23/09/1989 | FC Penafiel | - | Sporting CP | 0:0 | ||||
| 7. Round | 28/10/1989 | Sporting Braga | - | FC Penafiel | 3:0 | ||||
| 8. Round | 04/11/1989 | FC Penafiel | - | CD Feirense | 2:0 | ||||
| 13. Round | 22/12/1989 | Os Belenenses | - | FC Penafiel | 2:1 | ||||
| 16. Round | 13/01/1990 | FC Penafiel | - | SC Beira-Mar | 0:0 | ||||
| 20. Round | 17/02/1990 | FC Penafiel | - | Portimonense SC | 2:0 | ||||
| 27. Round | 07/04/1990 | Boavista | - | FC Penafiel | 3:0 |
Portugal