| 3. Round | 03/04/2019 | Dinamo-Auto | - | FC Sheriff | 0:4 |  |
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| 5. Round | 12/04/2019 | FC Sfîntul Gheorghe | - | FC Sheriff | 0:3 | ||||
| 7. Round | 26/04/2019 | CS Petrocub | - | FC Sheriff | 1:0 | ||||
| 10. Round | 18/05/2019 | FC Sheriff | - | Dinamo-Auto | 3:0 | ||||
| 11. Round | 26/05/2019 | FC Milsami | - | FC Sheriff | 1:2 | ||||
| 12. Round | 31/05/2019 | FC Sheriff | - | FC Sfîntul Gheorghe | 5:0 | |
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| 15. Round | 29/06/2019 | FC Sheriff | - | Speranţa Nisporeni | 3:0 |
Serbia