| 1. Round | 20/08/1999 | CD Santa Clara | - | Sporting CP | 2:2 |  |
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| 2. Round | 28/08/1999 | CS Marítimo | - | CD Santa Clara | 0:0 | |
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| 12. Round | 27/11/1999 | CD Santa Clara | - | Sporting Braga | 1:2 | ||||
| 13. Round | 02/12/1999 | FC Porto | - | CD Santa Clara | 1:0 | ||||
| 14. Round | 11/12/1999 | CD Santa Clara | - | Campomaiorense | 2:2 | ||||
| 22. Round | 19/02/2000 | CD Santa Clara | - | Rio Ave FC | 1:0 |
Brazil