3. Round | 13/03/2021 | FC Kuressaare | - | Tulevik Viljandi | 2:3 | ||||
2. Round | 20/03/2021 | FC Kuressaare | - | JK Tammeka | 1:3 | ||||
5. Round | 07/04/2021 | FC Kuressaare | - | JK Nõmme Kalju | 0:2 | ||||
6. Round | 10/04/2021 | Paide Linnameeskond | - | FC Kuressaare | 1:0 | ||||
8. Round | 21/04/2021 | FC Kuressaare | - | Pärnu JK Vaprus | 2:1 | ||||
9. Round | 25/04/2021 | JK Narva Trans | - | FC Kuressaare | 2:0 | ||||
10. Round | 30/04/2021 | FC Kuressaare | - | FC Flora | 0:4 | ||||
11. Round | 04/05/2021 | FC Kuressaare | - | Paide Linnameeskond | 2:2 | ||||
13. Round | 15/05/2021 | Tulevik Viljandi | - | FC Kuressaare | 1:2 | ||||
14. Round | 18/05/2021 | FC Kuressaare | - | JK Narva Trans | 1:2 | ||||
15. Round | 26/05/2021 | FC Kuressaare | - | FCI Levadia | 2:3 | ||||
18. Round | 30/07/2021 | Pärnu JK Vaprus | - | FC Kuressaare | 2:1 | ||||
19. Round | 07/08/2021 | FCI Levadia | - | FC Kuressaare | 3:0 | ||||
20. Round | 14/08/2021 | FC Kuressaare | - | FC Flora | 1:0 |