| 3. Round | 23/05/2020 | JK Nõmme Kalju | - | Tallinna JK Legion | 1:2 | ||||
| 9. Round | 27/06/2020 | Paide Linnameeskond | - | Tallinna JK Legion | 2:0 | ||||
| 10. Round | 30/06/2020 | Tallinna JK Legion | - | JK Tallinna Kalev | 0:0 | ||||
| 11. Round | 08/07/2020 | JK Tammeka | - | Tallinna JK Legion | 1:3 | ||||
| 12. Round | 12/07/2020 | FCI Levadia | - | Tallinna JK Legion | 4:0 |  |
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| 13. Round | 17/07/2020 | Tallinna JK Legion | - | FC Kuressaare | 1:1 | |
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| 14. Round | 25/07/2020 | JK Narva Trans | - | Tallinna JK Legion | 2:0 | ||||
| 15. Round | 01/08/2020 | Tallinna JK Legion | - | Paide Linnameeskond | 0:3 | |
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| 23. Round | 29/08/2020 | FC Flora | - | Tallinna JK Legion | 1:0 | ||||
| 20. Round | 13/09/2020 | Tallinna JK Legion | - | JK Narva Trans | 2:1 | |
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| 22. Round | 27/09/2020 | Tallinna JK Legion | - | JK Tammeka | 3:1 | |
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| 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 | |
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| 26. Round | 31/10/2020 | Tulevik Viljandi | - | Tallinna JK Legion | 0:0 | |
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| 27. Round | 14/11/2020 | Tallinna JK Legion | - | FCI Levadia | 1:2 | |
Estonia