Head to Head
| Portugal U23 League | 2019/12/07 14:00 | Guimaraes U23 v Benfica U23 | L | 0-4 |
| Portugal U23 League | 2019/08/27 10:00 | Benfica U23 v Guimaraes U23 | L | 4-2 |
| Portugal U23 League | 2018/12/22 11:00 | Benfica U23 v Guimaraes U23 | D | 1-1 |
| Portugal U23 League | 2018/11/24 11:00 | Guimaraes U23 v Benfica U23 | L | 1-3 |
Home History
| Portugal U23 League | 2020/12/22 15:00 | Guimaraes U23 v Academica Coimbra SF U23 | W | 4-2 |
| Portugal U23 League | 2020/12/19 11:00 | Braga U23 v Guimaraes U23 | D | 0-0 |
| Portugal U23 League | 2020/12/05 11:00 | Guimaraes U23 v Rio Ave U23 | L | 0-2 |
| Portugal U23 League | 2020/11/27 14:30 | Leixoes U23 v Guimaraes U23 | L | 5-1 |
| Portugal U23 League | 2020/11/21 11:00 | Guimaraes U23 v Famalicao U23 | W | 2-0 |
| Portugal U23 League | 2020/11/17 15:00 | Academica Coimbra SF U23 v Guimaraes U23 | W | 1-3 |
| Portugal U23 League | 2020/11/14 11:00 | Rio Ave U23 v Guimaraes U23 | D | 1-1 |
| Portugal U23 League | 2020/11/10 17:00 | Boavista U23 v Guimaraes U23 | D | 0-0 |
Away History
| Portugal U23 League | 2020/12/18 11:00 | Benfica U23 v Estoril U23 | L | 1-3 |
| Portugal U23 League | 2020/12/11 11:00 | Cova de Piedade U23 v Benfica U23 | W | 0-5 |
| Portugal U23 League | 2020/12/05 11:00 | Benfica U23 v Maritimo U23 | D | 3-3 |
| Portugal U23 League | 2020/12/01 12:00 | Sporting U23 v Benfica U23 | W | 0-3 |
| Portugal U23 League | 2020/11/20 15:00 | Benfica U23 v Portimonense U23 | W | 1-0 |
| Portugal U23 League | 2020/11/05 14:00 | Belenenses U23 v Benfica U23 | L | 2-1 |
| Portugal U23 League | 2020/10/23 13:45 | Estoril U23 v Benfica U23 | L | 2-0 |
| Portugal U23 League | 2020/10/17 15:00 | Benfica U23 v Cova de Piedade U23 | W | 4-1 |