| 2. Round | 19/05/2020 | FC Kuressaare | - | JK Nõmme Kalju | 0:2 |  |
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| 11. Round | 07/07/2020 | JK Nõmme Kalju | - | FC Kuressaare | 1:0 | ||||
| 12. Round | 11/07/2020 | FC Kuressaare | - | JK Tammeka | 2:4 | ||||
| 16. Round | 07/08/2020 | FC Flora | - | FC Kuressaare | 3:0 | ||||
| 18. Round | 22/08/2020 | FC Kuressaare | - | Paide Linnameeskond | 0:4 | ||||
| 20. Round | 13/09/2020 | FC Kuressaare | - | FCI Levadia | 1:5 | ||||
| 21. Round | 19/09/2020 | FC Kuressaare | - | Tallinna JK Legion | 2:2 | ||||
| 22. Round | 26/09/2020 | Tulevik Viljandi | - | FC Kuressaare | 1:1 | ||||
| 23. Round | 03/10/2020 | FC Kuressaare | - | JK Tallinna Kalev | 0:1 | ||||
| 24. Round | 18/10/2020 | JK Tammeka | - | FC Kuressaare | 4:2 | ||||
| 25. Round | 25/10/2020 | FC Kuressaare | - | FC Flora | 0:4 | ||||
| 26. Round | 01/11/2020 | Paide Linnameeskond | - | FC Kuressaare | 6:2 | ||||
| 27. Round | 07/11/2020 | FC Kuressaare | - | JK Nõmme Kalju | 1:1 |
Denmark