| 9. Round | 12/09/2020 | Dacia Buiucani | - | FC Sheriff | 0:3 | ||||
| 12. Round | 28/09/2020 | FC Sheriff | - | FC Codru Lozova | 6:0 | ||||
| 13. Round | 03/10/2020 | FC Zimbru | - | FC Sheriff | 0:4 |  |
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| 14. Round | 17/10/2020 | FC Sheriff | - | FC Milsami | 1:0 | ||||
| 15. Round | 20/10/2020 | Dinamo-Auto | - | FC Sheriff | 1:2 | ||||
| 16. Round | 24/10/2020 | FC Sheriff | - | FC Floreşti | 5:0 | ||||
| 17. Round | 01/11/2020 | CS Petrocub | - | FC Sheriff | 1:0 | ||||
| 18. Round | 07/11/2020 | FC Sheriff | - | Dacia Buiucani | 0:0 |  |
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| 19. Round | 21/11/2020 | FC Sheriff | - | Speranţa Nisporeni | 3:0 | ||||
| 20. Round | 25/11/2020 | FC Sfîntul Gheorghe | - | FC Sheriff | 0:2 | ||||
| 21. Round | 28/11/2020 | FC Codru Lozova | - | FC Sheriff | 1:2 | ||||
| 11. Round | 20/02/2021 | FC Sheriff | - | FC Sfîntul Gheorghe | 4:1 | ||||
| 31. Round | 08/05/2021 | FC Zimbru | - | FC Sheriff | 0:1 | ||||
| 32. Round | 12/05/2021 | FC Sheriff | - | FC Milsami | 6:0 | ||||
| 33. Round | 15/05/2021 | Dinamo-Auto | - | FC Sheriff | 0:7 | ||||
| 34. Round | 19/05/2021 | FC Sheriff | - | FC Floreşti | 3:0 |
Trinidad & Tobago