2. Round | 29/08/1999 | Sporting CP | - | Vitória Setúbal | 2:1 | ||||
3. Round | 11/09/1999 | SC Farense | - | Sporting CP | 0:3 | ||||
4. Round | 19/09/1999 | Sporting CP | - | Estrela Amadora | 1:1 | ||||
5. Round | 24/09/1999 | Gil Vicente | - | Sporting CP | 1:1 | ||||
18. Round | 21/01/2000 | Sporting CP | - | CD Santa Clara | 4:1 |