| 2019-01-20 17:00:0020/01/2019 |   Académica vs UD Oliveirense | 17:00:0017:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Cidade de Coimbra |
| 2019-01-30 16:00:0030/01/2019 |  UD Oliveirense vs Ac. Viseu | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-02-03 16:00:0003/02/2019 |  Cova da Piedade vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Municipal José Martins Vieira |
| 2019-02-10 16:00:0010/02/2019 |  UD Oliveirense vs CD Mafra | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-02-17 16:00:0017/02/2019 |  FC Porto B vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Municipal Dr. Jorge Sampaio |
| 2019-02-24 16:00:0024/02/2019 |  UD Oliveirense vs Leixoes | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-03-03 16:00:0003/03/2019 |  Braga B vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal 1º de Maio |
| 2019-03-10 16:00:0010/03/2019 |  UD Oliveirense vs Sp. Covilhã | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-03-17 16:00:0017/03/2019 |  Varzim vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio do Varzim SC |
| 2019-03-31 16:00:0031/03/2019 |  UD Oliveirense vs V. Guimarães B | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-04-07 16:00:0007/04/2019 |  Paços de Ferreira vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio da Capital do Móvel |
| 2019-04-14 16:00:0014/04/2019 |  UD Oliveirense vs Benfica B | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-04-20 16:00:0020/04/2019 |  Estoril Praia vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio António Coimbra da Mota |
| 2019-04-28 16:00:0028/04/2019 |  UD Oliveirense vs SC Farense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-05-05 16:00:0005/05/2019 |  FC Penafiel vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Municipal 25 de Abril |
| 2019-05-12 16:00:0012/05/2019 |  FC Famalicão vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Municipal de Famalicão |
| 2019-05-19 16:00:0019/05/2019 |  UD Oliveirense vs Arouca | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
