| 1. Round | 03/07/2020 | FC Sheriff | - | Speranţa Nisporeni | 2:0 |  |
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| 2. Round | 08/07/2020 | FC Sfîntul Gheorghe | - | FC Sheriff | 0:1 |  |
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| 3. Round | 11/07/2020 | FC Sheriff | - | FC Codru Lozova | 6:0 | |
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| 4. Round | 17/07/2020 | FC Sheriff | - | FC Zimbru | 2:0 | ||||
| 7. Round | 01/08/2020 | FC Floreşti | - | FC Sheriff | 0:1 | ||||
| 8. Round | 05/08/2020 | FC Sheriff | - | CS Petrocub | 4:1 | ||||
| 9. Round | 12/09/2020 | Dacia Buiucani | - | FC Sheriff | 0:3 | ||||
| 10. Round | 18/09/2020 | Speranţa Nisporeni | - | FC Sheriff | 1:2 | ||||
| 14. Round | 17/10/2020 | FC Sheriff | - | FC Milsami | 1:0 | ||||
| 15. Round | 20/10/2020 | Dinamo-Auto | - | FC Sheriff | 1:2 | |
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| 16. Round | 24/10/2020 | FC Sheriff | - | FC Floreşti | 5:0 | |
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| 17. Round | 01/11/2020 | CS Petrocub | - | FC Sheriff | 1:0 | ||||
| 18. Round | 07/11/2020 | FC Sheriff | - | Dacia Buiucani | 0:0 | ||||
| 19. Round | 21/11/2020 | FC Sheriff | - | Speranţa Nisporeni | 3:0 | ||||
| 20. Round | 25/11/2020 | FC Sfîntul Gheorghe | - | FC Sheriff | 0:2 | |
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| 21. Round | 28/11/2020 | FC Codru Lozova | - | FC Sheriff | 1:2 | |
Ukraine