| 1. Round | 16/03/2019 | FC Sheriff | - | Speranţa Nisporeni | 1:0 |  |
|||
| 2. Round | 29/03/2019 | FC Sheriff | - | FC Zimbru | 3:0 | ||||
| 3. Round | 03/04/2019 | Dinamo-Auto | - | FC Sheriff | 0:4 | |
|||
| 4. Round | 07/04/2019 | FC Sheriff | - | FC Milsami | 0:1 | ||||
| 24. Round | 06/10/2019 | FC Sheriff | - | Dinamo-Auto | 2:0 |
Ukraine