| 2018-11-18 17:00:0018/11/2018 |   UD Oliveirense vs FC Famalicão | 17:00:0017:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2018-12-02 16:00:0002/12/2018 |  V. Guimarães B vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio D. Afonso Henriques |
| 2018-12-09 16:00:0009/12/2018 |  UD Oliveirense vs Paços de Ferreira | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2018-12-16 16:00:0016/12/2018 |  Benfica B vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Caixa Futebol Campus |
| 2018-12-23 16:00:0023/12/2018 |  UD Oliveirense vs Estoril Praia | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-01-02 16:00:0002/01/2019 |  SC Farense vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio de São Luís |
| 2019-01-06 16:00:0006/01/2019 |  UD Oliveirense vs FC Penafiel | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Aveiro |
| 2019-01-13 16:00:0013/01/2019 |  Arouca vs UD Oliveirense | 16:00:0016:00 | LEDMAN Liga Pro | 2018/2019 | Estádio Municipal de Arouca |
| 2019-01-19 16:00:0019/01/2019 |  Académica vs UD Oliveirense | 16:00:0016:00 | 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 |
