| 1. Ronde | 10.08.2019 | SL Benfica [A-jun] | - | Vitória Setúbal [A-jun] | 1:0 |  |
|||
| 2. Ronde | 18.08.2019 | CD Tondela [A-jun] | - | SL Benfica [A-jun] | 0:2 | ||||
| 3. Ronde | 24.08.2019 | SL Benfica [A-jun] | - | GD Estoril [A-jun] | 4:0 | ||||
| 9. Ronde | 20.10.2019 | Sporting CP [A-jun] | - | SL Benfica [A-jun] | 2:2 | ||||
| 11. Ronde | 02.11.2019 | FC Alverca [A-jun] | - | SL Benfica [A-jun] | 1:4 |
Portugal