| 1. Round | 08/03/2020 | JK Tammeka | - | Tulevik Viljandi | 2:1 | ||||
| 2. Round | 19/05/2020 | Paide Linnameeskond | - | Tulevik Viljandi | 1:2 | ||||
| 3. Round | 24/05/2020 | Tulevik Viljandi | - | FCI Levadia | 1:3 | ||||
| 4. Round | 31/05/2020 | Tulevik Viljandi | - | JK Nõmme Kalju | 0:6 | ||||
| 5. Round | 03/06/2020 | JK Narva Trans | - | Tulevik Viljandi | 0:2 | ||||
| 6. Round | 07/06/2020 | Tulevik Viljandi | - | FC Kuressaare | 5:0 | ||||
| 7. Round | 12/06/2020 | FC Flora | - | Tulevik Viljandi | 3:0 | ||||
| 8. Round | 16/06/2020 | Tallinna JK Legion | - | Tulevik Viljandi | 0:2 |  |
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| 9. Round | 27/06/2020 | Tulevik Viljandi | - | JK Tallinna Kalev | 2:1 | ||||
| 11. Round | 08/07/2020 | Tulevik Viljandi | - | FC Flora | 2:1 | ||||
| 15. Round | 02/08/2020 | FCI Levadia | - | Tulevik Viljandi | 5:1 | ||||
| 22. Round | 26/09/2020 | Tulevik Viljandi | - | FC Kuressaare | 1:1 | |
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| 19. Round | 04/10/2020 | FC Flora | - | Tulevik Viljandi | 2:1 | ||||
| 24. Round | 17/10/2020 | FCI Levadia | - | Tulevik Viljandi | 2:0 | ||||
| 25. Round | 24/10/2020 | Tulevik Viljandi | - | JK Tammeka | 0:1 | |
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| 26. Round | 31/10/2020 | Tulevik Viljandi | - | Tallinna JK Legion | 0:0 | ||||
| 27. Round | 08/11/2020 | JK Tallinna Kalev | - | Tulevik Viljandi | 1:0 | |
Estonia