| 4. Round | 04/04/2021 | Tulevik Viljandi | - | FCI Levadia | 0:4 | ||||
| 10. Round | 01/05/2021 | Tulevik Viljandi | - | JK Nõmme Kalju | 1:3 | ||||
| 11. Round | 05/05/2021 | FCI Levadia | - | Tulevik Viljandi | 4:1 | ||||
| 5. Round | 25/06/2021 | Tulevik Viljandi | - | Pärnu JK Vaprus | 3:1 | ||||
| 1. Round | 30/06/2021 | JK Nõmme Kalju | - | Tulevik Viljandi | 5:1 | ||||
| 17. Round | 17/07/2021 | Tulevik Viljandi | - | JK Narva Trans | 0:1 | ||||
| 18. Round | 31/07/2021 | Tulevik Viljandi | - | JK Tammeka | 5:3 | ||||
| 19. Round | 07/08/2021 | Paide Linnameeskond | - | Tulevik Viljandi | 3:1 | ||||
| 20. Round | 15/08/2021 | JK Nõmme Kalju | - | Tulevik Viljandi | 3:1 | ||||
| 21. Round | 20/08/2021 | Tulevik Viljandi | - | Pärnu JK Vaprus | 1:0 | ||||
| 23. Round | 11/09/2021 | JK Narva Trans | - | Tulevik Viljandi | 1:0 | ||||
| 24. Round | 18/09/2021 | Tallinna JK Legion | - | Tulevik Viljandi | 3:1 |  |
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| 25. Round | 26/09/2021 | Tulevik Viljandi | - | FC Flora | 2:2 | |
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| 26. Round | 03/10/2021 | FC Kuressaare | - | Tulevik Viljandi | 1:0 | ||||
| 27. Round | 16/10/2021 | Tulevik Viljandi | - | FCI Levadia | 3:2 |
Estonia