Head to Head
| Portugal U23 League | 2019/02/02 11:00 | Guimaraes U23 v Estoril U23 | W | 1-3 |
| Portugal U23 League | 2018/10/30 15:00 | Estoril U23 v Guimaraes U23 | D | 1-1 |
Home History
| Portugal U23 League | 2019/08/31 10:00 | Benfica U23 v Estoril U23 | L | 1-0 |
| Portugal U23 League | 2019/08/28 10:00 | Estoril U23 v Feirense U23 | W | 1-0 |
| Portugal U23 League | 2019/08/23 15:00 | Belenenses U23 v Estoril U23 | L | 2-1 |
| Portugal U23 League | 2019/08/19 16:45 | Estoril U23 v Rio Ave U23 | D | 2-2 |
| Portugal U23 League | 2019/08/12 10:00 | Leixoes U23 v Estoril U23 | D | 2-2 |
| Europe Friendlies | 2019/08/03 10:00 | SU Sintrense v Estoril U23 | W | 2-4 |
| Portugal U23 League | 2019/05/04 10:00 | Benfica U23 v Estoril U23 | L | 4-3 |
| Portugal U23 League | 2019/05/01 10:00 | Rio Ave U23 v Estoril U23 | W | 1-2 |
Away History
| Portugal U23 League | 2019/08/31 15:00 | Guimaraes U23 v Maritimo U23 | W | 1-0 |
| Portugal U23 League | 2019/08/27 10:00 | Benfica U23 v Guimaraes U23 | L | 4-2 |
| Portugal U23 League | 2019/08/23 17:00 | Guimaraes U23 v Sporting U23 | L | 0-6 |
| Portugal U23 League | 2019/08/19 10:00 | Feirense U23 v Guimaraes U23 | D | 1-1 |
| Portugal U23 League | 2019/08/12 16:45 | Guimaraes U23 v CD Aves U23 | D | 2-2 |
| Europe Friendlies | 2019/07/27 09:00 | Amarante v Guimaraes U23 | D | 2-2 |
| Portugal U23 League | 2019/05/01 10:00 | Guimaraes U23 v Feirense U23 | D | 1-1 |
| Portugal U23 League | 2019/04/27 10:00 | Belenenses U23 v Guimaraes U23 | D | 1-1 |