| 2. Round | 19/08/2023 | GD Estoril [Youth] | - | SL Benfica [Youth] | 0:4 |  |
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| 5. Round | 16/09/2023 | SL Benfica [Youth] | - | Sporting CP [Youth] | 1:2 | |
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| 6. Round | 23/09/2023 | Os Belenenses [Youth] | - | SL Benfica [Youth] | 2:1 | ||||
| 7. Round | 30/09/2023 | SL Benfica [Youth] | - | Vitória Setúbal [Youth] | 2:2 | ||||
| 8. Round | 07/10/2023 | Académica de Coimbra [Youth] | - | SL Benfica [Youth] | 1:3 | ||||
| 9. Round | 21/10/2023 | SL Benfica [Youth] | - | SC Farense [Youth] | 5:0 | ||||
| 10. Round | 27/10/2023 | FC Alverca [Youth] | - | SL Benfica [Youth] | 1:2 | |
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| 11. Round | 01/11/2023 | SL Benfica [Youth] | - | SC Beira-Mar [Youth] | 4:1 | ||||
| 12. Round | 05/11/2023 | SC Lusitânia [Youth] | - | SL Benfica [Youth] | 0:2 | ||||
| 13. Round | 12/11/2023 | SL Benfica [Youth] | - | GD Estoril [Youth] | 4:0 | |
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| 20. Round | 13/01/2024 | SC Farense [Youth] | - | SL Benfica [Youth] | 1:0 | ||||
| 21. Round | 19/01/2024 | SL Benfica [Youth] | - | FC Alverca [Youth] | 3:0 | ||||
| 22. Round | 28/01/2024 | SC Beira-Mar [Youth] | - | SL Benfica [Youth] | 0:2 |
Portugal