| 11. Ronde | 02.11.2019 | UD Vilafranquense [A-jun] | - | Os Belenenses [A-jun] | 1:5 | ||||
| 18. Ronde | 04.01.2020 | SG Sacavenense [A-jun] | - | Os Belenenses [A-jun] | 0:2 |  |
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| 19. Ronde | 11.01.2020 | Os Belenenses [A-jun] | - | SL Benfica [A-jun] | 0:3 | ||||
| 20. Ronde | 18.01.2020 | Os Belenenses [A-jun] | - | União Leiria [A-jun] | 6:0 | ||||
| 21. Ronde | 25.01.2020 | Sporting CP [A-jun] | - | Os Belenenses [A-jun] | 5:1 | ||||
| 22. Ronde | 01.02.2020 | Os Belenenses [A-jun] | - | UD Vilafranquense [A-jun] | 2:1 |
Portugal