| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 19.10.2008 | 3. Round | 3. Rd | A | ![]() | Fabril do Barreiro | W | 1:0 |
| 09.11.2008 | 4. Round | 4. Rd | H | ![]() | SC Beira-Mar | W | 2:0 |
| 13.12.2008 | Round of 16 | Rd of 16 | A | ![]() | Amadora | L | 0:1aet |
CD Olivais e Moscavide


| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 19.10.2008 | 3. Round | 3. Rd | A | ![]() | Fabril do Barreiro | W | 1:0 |
| 09.11.2008 | 4. Round | 4. Rd | H | ![]() | SC Beira-Mar | W | 2:0 |
| 13.12.2008 | Round of 16 | Rd of 16 | A | ![]() | Amadora | L | 0:1aet |