Home History
| Taça de Portugal | 2019/09/29 14:00 | Sintra Football v Amarante | W | 2-0 |
| Portugal - Campeonato Nacional | 2019/09/22 14:00 | Grupo Sportivo Loures v Sintra Football | W | 3-4 |
| Portugal - Campeonato Nacional | 2019/09/15 14:00 | Sintra Football v Amora | D | 1-1 |
| Taça de Portugal | 2019/09/07 15:59 | Sintra Football v Grupo Sportivo Loures | W | 1-0 |
| Portugal - Campeonato Nacional | 2019/09/01 15:00 | Sacavenense v Sintra Football | D | 2-2 |
| Portugal - Campeonato Nacional | 2019/08/25 16:00 | Sintra Football v Fabril Barreiro | W | 3-0 |
| Portugal - Campeonato Nacional | 2019/08/18 16:00 | SU 1 Dezembro v Sintra Football | L | 1-0 |
| Europa - Amigáveis | 2019/08/03 16:00 | Sintra Football v Grupo Sportivo Loures | D | 0-0 |
Away History
| Taça de Portugal | 2019/09/29 14:00 | Sport Benfica e Castelo Branco v Olhanense | L | 3-2 |
| Portugal - Campeonato Nacional | 2019/09/22 14:00 | Olhanense v CF Esperança de Lagos | W | 4-1 |
| Portugal - Campeonato Nacional | 2019/09/14 15:00 | Louletano DC v Olhanense | L | 1-0 |
| Taça de Portugal | 2019/09/08 16:00 | Olhanense v FC Armacenenses | W | 1-0 |
| Portugal - Campeonato Nacional | 2019/09/01 16:00 | Olhanense v Real Sport Clube Queluz | W | 3-2 |
| Portugal - Campeonato Nacional | 2019/08/25 16:00 | SC Mineiro Aljustrelense v Olhanense | W | 1-3 |
| Portugal - Campeonato Nacional | 2019/08/18 16:00 | Olhanense v FC Armacenenses | W | 2-1 |
| Portugal - Campeonato Nacional | 2019/05/12 16:00 | Moura v Olhanense | W | 1-5 |
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