| 4. Round | 30/05/2020 | FC Flora | - | JK Tallinna Kalev | 3:0 | ||||
| 5. Round | 02/06/2020 | JK Tallinna Kalev | - | Tallinna JK Legion | 1:0 | ||||
| 6. Round | 06/06/2020 | FCI Levadia | - | JK Tallinna Kalev | 4:0 | ||||
| 7. Round | 14/06/2020 | JK Tallinna Kalev | - | JK Nõmme Kalju | 0:4 | ||||
| 8. Round | 17/06/2020 | JK Tallinna Kalev | - | FC Kuressaare | 0:2 | ||||
| 9. Round | 27/06/2020 | Tulevik Viljandi | - | JK Tallinna Kalev | 2:1 | ||||
| 10. Round | 30/06/2020 | Tallinna JK Legion | - | JK Tallinna Kalev | 0:0 | ||||
| 11. Round | 08/07/2020 | JK Tallinna Kalev | - | FCI Levadia | 0:4 | ||||
| 12. Round | 12/07/2020 | JK Nõmme Kalju | - | JK Tallinna Kalev | 2:0 | ||||
| 13. Round | 18/07/2020 | JK Tallinna Kalev | - | Tulevik Viljandi | 0:2 | ||||
| 14. Round | 27/07/2020 | FC Kuressaare | - | JK Tallinna Kalev | 2:2 | ||||
| 15. Round | 31/07/2020 | JK Tallinna Kalev | - | FC Flora | 0:3 | ||||
| 16. Round | 09/08/2020 | Paide Linnameeskond | - | JK Tallinna Kalev | 4:0 | ||||
| 17. Round | 16/08/2020 | JK Narva Trans | - | JK Tallinna Kalev | 1:0 |  |
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| 18. Round | 22/08/2020 | JK Tallinna Kalev | - | JK Tammeka | 0:2 |
Estonia