[1] Estoril U23 4-2 Portimonense U23 [8] 2023-08-29 15:00
Stadium: Estadio Antonio Coimbra da Mota Round: 4
Head to Head
| Portugal U23 Cup | 2023/05/06 10:00 | Estoril U23 v Portimonense U23 | W | 3-2 |
| 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 Cup | 2021/04/19 16:00 | Portimonense U23 v Estoril U23 | W | 2-3 |
| Portugal U23 Cup | 2021/04/12 14:30 | Estoril U23 v Portimonense U23 | W | 3-0 |
| Portugal U23 League | 2020/11/14 11:00 | Portimonense U23 v Estoril U23 | D | 1-1 |
| Portugal U23 League | 2020/09/12 15:00 | Estoril U23 v Portimonense U23 | W | 3-1 |
| Portugal U23 League | 2020/02/08 14:00 | Portimonense U23 v Estoril U23 | W | 1-2 |
| Portugal U23 League | 2019/11/09 11:00 | Estoril U23 v Portimonense U23 | W | 4-1 |
| Portugal U23 League | 2018/11/10 11:00 | Portimonense U23 v Estoril U23 | W | 2-4 |
| Portugal U23 League | 2018/08/18 11:00 | Estoril U23 v Portimonense U23 | W | 3-1 |