1. Round | 20/08/1999 | CD Santa Clara | - | Sporting CP | 2:2 | ||||
2. Round | 28/08/1999 | CS Marítimo | - | CD Santa Clara | 0:0 | ||||
3. Round | 11/09/1999 | CD Santa Clara | - | SL Benfica | 0:3 | ||||
5. Round | 25/09/1999 | Rio Ave FC | - | CD Santa Clara | 0:5 | ||||
9. Round | 30/10/1999 | Gil Vicente | - | CD Santa Clara | 3:1 | ||||
10. Round | 07/11/1999 | CD Santa Clara | - | Boavista | 0:1 | ||||
12. Round | 27/11/1999 | CD Santa Clara | - | Sporting Braga | 1:2 | ||||
18. Round | 21/01/2000 | Sporting CP | - | CD Santa Clara | 4:1 | ||||
29. Round | 08/04/2000 | Sporting Braga | - | CD Santa Clara | 3:1 | ||||
34. Round | 13/05/2000 | CD Santa Clara | - | Vitória Guimarães | 3:2 |