| 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 |
