| 2019-07-28 19:00:3228/07/2019 |   Oliveirense vs Mafra | 19:00:3219:00 | Taça da Liga | 2019/2020 | Municipal Dr. Jorge Sampaio |
| 2019-08-11 16:00:0011/08/2019 |  Varzim vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2019-08-18 16:00:0018/08/2019 |  UD Oliveirense vs Sp. Covilhã | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2019-08-25 16:00:0025/08/2019 |  Benfica B vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2019-09-01 16:00:0001/09/2019 |  UD Oliveirense vs SC Farense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2019-09-15 16:00:0015/09/2019 |  Casa Pia vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2019-09-22 16:00:0022/09/2019 |  UD Oliveirense vs FC Porto B | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2019-10-27 16:00:0027/10/2019 |  Estoril Praia vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2019-10-30 16:00:0030/10/2019 |  Vilafranquense vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2019-11-03 16:00:0003/11/2019 |  UD Oliveirense vs Cova da Piedade | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2019-11-10 16:00:0010/11/2019 |  Leixões vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2019-12-01 16:00:0001/12/2019 |  UD Oliveirense vs Ac. Viseu | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2019-12-08 16:00:0008/12/2019 |  GD Chaves vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2019-12-15 16:00:0015/12/2019 |  UD Oliveirense vs FC Penafiel | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2019-12-29 16:00:0029/12/2019 |  Académica vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-01-05 16:00:0005/01/2020 | UD Oliveirense vs CD Mafra | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-01-11 16:00:0011/01/2020 |  CD Nacional vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-01-18 16:00:0018/01/2020 |  UD Oliveirense vs CD Feirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-01-26 16:00:0026/01/2020 | UD Oliveirense vs Varzim | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-02-02 16:00:0002/02/2020 | Sp. Covilhã vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-02-09 16:00:0009/02/2020 | UD Oliveirense vs Benfica B | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-02-15 16:00:0015/02/2020 | SC Farense vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-02-23 16:00:0023/02/2020 | UD Oliveirense vs Casa Pia | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-03-01 16:00:0001/03/2020 | FC Porto B vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-03-08 16:00:0008/03/2020 | UD Oliveirense vs Estoril Praia | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-03-15 16:00:0015/03/2020 | UD Oliveirense vs Vilafranquense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-03-22 16:00:0022/03/2020 | Cova da Piedade vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-04-05 16:00:0005/04/2020 | UD Oliveirense vs Leixões | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-04-11 16:00:0011/04/2020 | Ac. Viseu vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-04-19 16:00:0019/04/2020 | UD Oliveirense vs GD Chaves | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-04-22 16:00:0022/04/2020 | FC Penafiel vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-04-26 16:00:0026/04/2020 | UD Oliveirense vs Académica | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-05-03 16:00:0003/05/2020 | CD Mafra vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-05-10 16:00:0010/05/2020 | UD Oliveirense vs CD Nacional | 16:00:0016:00 | Liga Pro | 2019/2020 | |
| 2020-05-17 16:00:0017/05/2020 | CD Feirense vs UD Oliveirense | 16:00:0016:00 | Liga Pro | 2019/2020 | |
