Home History
| Portugal - Liga de Sub23 | 2019/09/28 15:00 | Vitória de Guimarães Sub23 v Portimonense Sub23 | W | 1-2 |
| Portugal - Liga de Sub23 | 2019/09/21 10:00 | Portimonense Sub23 v CS Marítimo Sub23 | D | 2-2 |
| Portugal - Liga de Sub23 | 2019/09/14 10:00 | Sporting CP Sub23 v Portimonense Sub23 | L | 4-3 |
| Portugal - Liga de Sub23 | 2019/09/07 15:00 | FC Famalicão Sub23 v Portimonense Sub23 | W | 2-3 |
| Portugal - Liga de Sub23 | 2019/08/31 10:00 | Portimonense Sub23 v CD Aves Sub23 | D | 2-2 |
| Portugal - Liga de Sub23 | 2019/08/27 15:00 | SC Braga Sub23 v Portimonense Sub23 | L | 2-1 |
| Portugal - Liga de Sub23 | 2019/08/24 16:00 | Portimonense Sub23 v Vitória de Setúbal Sub23 | D | 2-2 |
| Portugal - Liga de Sub23 | 2019/08/20 09:30 | Associação Académica de Coimbra SF Sub23 v Portimonense Sub23 | W | 2-3 |
Away History
| Portugal - Liga de Sub23 | 2019/09/29 10:00 | Leixões SC Sub23 v FC Famalicão Sub23 | W | 2-1 |
| Portugal - Liga de Sub23 | 2019/09/24 10:00 | CS Marítimo Sub23 v Leixões SC Sub23 | L | 4-1 |
| Portugal - Liga de Sub23 | 2019/09/19 15:00 | Leixões SC Sub23 v Sporting CP Sub23 | L | 1-2 |
| Portugal - Liga de Sub23 | 2019/09/14 13:00 | CD Aves Sub23 v Leixões SC Sub23 | L | 3-1 |
| Portugal - Liga de Sub23 | 2019/08/31 16:00 | Leixões SC Sub23 v SC Braga Sub23 | D | 0-0 |
| Portugal - Liga de Sub23 | 2019/08/27 16:45 | Vitória de Setúbal Sub23 v Leixões SC Sub23 | D | 2-2 |
| Portugal - Liga de Sub23 | 2019/08/24 10:00 | Leixões SC Sub23 v Associação Académica de Coimbra SF Sub23 | W | 3-1 |
| Portugal - Liga de Sub23 | 2019/08/20 17:00 | Cova da Piedade Sub23 v Leixões SC Sub23 | W | 0-2 |