Stadium: Estadio Antonio Coimbra da Mota Round: 1
| Portugal U23 League | 2022/11/29 16:00 | Estoril U23 v Portimonense U23 | W | 2-0 |
| Portugal U23 League | 2022/09/05 14:00 | Portimonense U23 v Estoril U23 | D | 2-2 |
| Portugal U23 League | 2022/08/16 16:00 | Portimonense U23 v Estoril U23 | W | 0-1 |
| Portugal U23 Cup | 2022/04/27 16:00 | Estoril U23 v Portimonense U23 | W | 2-1 |
| Portugal U23 League | 2022/04/05 15:00 | Estoril U23 v Portimonense U23 | W | 5-1 |
| Portugal U23 League | 2022/02/05 15:00 | Portimonense U23 v Estoril U23 | L | 3-1 |
| Portugal U23 League | 2021/11/20 11:00 | Portimonense U23 v Estoril U23 | D | 1-1 |
| Portugal U23 League | 2021/09/10 16:00 | Estoril U23 v Portimonense U23 | W | 4-0 |
| Portugal U23 League | 2023/01/17 14:00 | Sporting U23 v Estoril U23 | L | 3-2 |
| Portugal U23 League | 2023/01/06 17:00 | Estoril U23 v Benfica U23 | W | 2-0 |
| Portugal U23 League | 2022/12/13 10:00 | Estoril U23 v CD Mafra U23 | D | 2-2 |
| Portugal U23 League | 2022/12/06 11:00 | SC Farense U23 v Estoril U23 | L | 4-1 |
| Portugal U23 League | 2022/11/29 16:00 | Estoril U23 v Portimonense U23 | W | 2-0 |
| Portugal U23 League | 2022/11/20 11:00 | Estrela Amadora U23 v Estoril U23 | D | 0-0 |
| Portugal U23 League | 2022/11/07 11:00 | Estoril U23 v Sporting U23 | W | 5-1 |
| Portugal U23 League | 2022/10/17 12:00 | Benfica U23 v Estoril U23 | L | 3-1 |
| Portugal U23 League | 2023/01/17 14:00 | Portimonense U23 v Benfica U23 | D | 3-3 |
| Portugal U23 League | 2023/01/10 11:00 | Estrela Amadora U23 v Portimonense U23 | L | 2-1 |
| Portugal U23 League | 2023/01/04 15:00 | Portimonense U23 v CD Mafra U23 | W | 3-2 |
| Portugal U23 League | 2022/12/19 11:00 | SC Farense U23 v Portimonense U23 | L | 2-1 |
| Portugal U23 League | 2022/12/06 11:00 | Portimonense U23 v Sporting U23 | W | 3-2 |
| Portugal U23 League | 2022/11/29 16:00 | Estoril U23 v Portimonense U23 | L | 2-0 |
| Portugal U23 League | 2022/11/07 15:00 | Benfica U23 v Portimonense U23 | L | 1-0 |
| Portugal U23 League | 2022/10/25 14:00 | Portimonense U23 v Estrela Amadora U23 | L | 0-3 |