| 15. Round | 01/08/2020 | Tallinna JK Legion | - | Paide Linnameeskond | 0:3 | ||||
| 16. Round | 08/08/2020 | Tulevik Viljandi | - | Tallinna JK Legion | 0:2 | ||||
| 17. Round | 15/08/2020 | Tallinna JK Legion | - | JK Nõmme Kalju | 0:6 | ||||
| 18. Round | 23/08/2020 | Tallinna JK Legion | - | FC Flora | 1:3 | ||||
| 23. Round | 29/08/2020 | FC Flora | - | Tallinna JK Legion | 1:0 | ||||
| 21. Round | 19/09/2020 | FC Kuressaare | - | Tallinna JK Legion | 2:2 | ||||
| 22. Round | 27/09/2020 | Tallinna JK Legion | - | JK Tammeka | 3:1 | ||||
| 19. Round | 04/10/2020 | JK Nõmme Kalju | - | Tallinna JK Legion | 1:1 | ||||
| 24. Round | 18/10/2020 | Tallinna JK Legion | - | Paide Linnameeskond | 0:2 | ||||
| 25. Round | 24/10/2020 | Tallinna JK Legion | - | JK Tallinna Kalev | 2:0 | ||||
| 26. Round | 31/10/2020 | Tulevik Viljandi | - | Tallinna JK Legion | 0:0 | ||||
| 27. Round | 14/11/2020 | Tallinna JK Legion | - | FCI Levadia | 1:2 |
Estonia