| 2018-09-30 16:00:2730 Setembro, 2018 |   CDF vs Oliveirense | 16:00:2716:00 | Taça de Portugal | 2018/2019 | Estádio Municipal de Fátima |
| 2018-10-07 16:00:007 Outubro, 2018 |  Leixoes vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio do Mar |
| 2018-10-28 16:00:0028 Outubro, 2018 |  UD Oliveirense vs Braga B | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2018-11-04 16:00:004 Novembro, 2018 |  Sp. Covilhã vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Municipal José dos Santos Pinto |
| 2018-11-11 16:00:0011 Novembro, 2018 |  UD Oliveirense vs Varzim | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2018-12-02 16:00:002 Dezembro, 2018 |  V. Guimarães B vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio D. Afonso Henriques |
| 2018-12-09 16:00:009 Dezembro, 2018 |  UD Oliveirense vs Paços de Ferreira | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2018-12-16 16:00:0016 Dezembro, 2018 |  Benfica B vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Caixa Futebol Campus |
| 2018-12-23 16:00:0023 Dezembro, 2018 |  UD Oliveirense vs Estoril Praia | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-01-02 16:00:002 Janeiro, 2019 |  SC Farense vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio de São Luís |
| 2019-01-06 16:00:006 Janeiro, 2019 |  UD Oliveirense vs FC Penafiel | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-01-09 16:00:009 Janeiro, 2019 |  UD Oliveirense vs FC Famalicão | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-01-13 16:00:0013 Janeiro, 2019 |  Arouca vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Arouca |
| 2019-01-19 16:00:0019 Janeiro, 2019 |  Académica vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Cidade de Coimbra |
| 2019-01-30 16:00:0030 Janeiro, 2019 |  UD Oliveirense vs Ac. Viseu | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-02-03 16:00:003 Fevereiro, 2019 |  Cova da Piedade vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Municipal José Martins Vieira |
| 2019-02-10 16:00:0010 Fevereiro, 2019 |  UD Oliveirense vs CD Mafra | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-02-17 16:00:0017 Fevereiro, 2019 |  FC Porto B vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Municipal Dr. Jorge Sampaio |
| 2019-02-24 16:00:0024 Fevereiro, 2019 | UD Oliveirense vs Leixoes | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-03-03 16:00:003 Março, 2019 | Braga B vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal 1º de Maio |
| 2019-03-10 16:00:0010 Março, 2019 | UD Oliveirense vs Sp. Covilhã | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-03-17 16:00:0017 Março, 2019 | Varzim vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio do Varzim SC |
| 2019-03-31 16:00:0031 Março, 2019 | UD Oliveirense vs V. Guimarães B | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-04-07 16:00:007 Abril, 2019 | Paços de Ferreira vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio da Capital do Móvel |
| 2019-04-14 16:00:0014 Abril, 2019 | UD Oliveirense vs Benfica B | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-04-20 16:00:0020 Abril, 2019 | Estoril Praia vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio António Coimbra da Mota |
| 2019-04-28 16:00:0028 Abril, 2019 | UD Oliveirense vs SC Farense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-05-05 16:00:005 Maio, 2019 | FC Penafiel vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Municipal 25 de Abril |
| 2019-05-12 16:00:0012 Maio, 2019 | FC Famalicão vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Municipal de Famalicão |
| 2019-05-19 16:00:0019 Maio, 2019 | UD Oliveirense vs Arouca | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
