Stadium: Estadio de Sao Miguel Round: 2
| Portugal U23 League | 2023/08/29 11:00 | Santa Clara U23 v Benfica U23 | W | 3-1 |
| Portugal U23 League | 2023/08/22 15:00 | Sporting U23 v Santa Clara U23 | L | 5-0 |
| Portugal U23 League | 2023/08/08 10:00 | Estoril U23 v Santa Clara U23 | D | 2-2 |
| Portugal U23 League | 2023/08/29 15:00 | CD Mafra U23 v Estrela Amadora U23 | W | 0-1 |
| Portugal U23 League | 2023/08/22 15:00 | Estrela Amadora U23 v SC Farense U23 | D | 0-0 |
| Portugal U23 League | 2023/08/08 14:00 | Estrela Amadora U23 v Benfica U23 | W | 2-1 |
| Portugal U23 Cup | 2023/05/29 17:00 | Estrela Amadora U23 v Braga U23 | L | 0-1 |
| Portugal U23 Cup | 2023/05/23 15:30 | Braga U23 v Estrela Amadora U23 | L | 2-0 |
| Portugal U23 League | 2023/05/16 16:00 | Estrela Amadora U23 v Estoril U23 | L | 0-2 |
| Portugal U23 Cup | 2023/05/09 16:30 | Portimonense U23 v Estrela Amadora U23 | W | 0-1 |
| Portugal U23 League | 2023/05/05 10:00 | Vizela U23 v Estrela Amadora U23 | W | 3-4 |