| 2. Ronde | 20.03.2021 | FCI Levadia | - | Tallinna JK Legion | 4:3 |  |
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| 3. Ronde | 28.03.2021 | Tallinna JK Legion | - | JK Nõmme Kalju | 0:1 | |
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| 1. Ronde | 04.04.2021 | Tallinna JK Legion | - | Paide Linnameeskond | 1:1 | |
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| 5. Ronde | 07.04.2021 | JK Narva Trans | - | Tallinna JK Legion | 0:0 | |
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| 6. Ronde | 11.04.2021 | Tallinna JK Legion | - | FC Flora | 1:2 | |
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| 8. Ronde | 20.04.2021 | JK Tammeka | - | Tallinna JK Legion | 0:1 | |
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| 10. Ronde | 01.05.2021 | Paide Linnameeskond | - | Tallinna JK Legion | 1:0 | ||||
| 12. Ronde | 08.05.2021 | FC Flora | - | Tallinna JK Legion | 2:1 | ||||
| 11. Ronde | 11.05.2021 | Tallinna JK Legion | - | Pärnu JK Vaprus | 7:1 | ||||
| 13. Ronde | 15.05.2021 | Tallinna JK Legion | - | JK Narva Trans | 3:0 | |
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| 15. Ronde | 25.05.2021 | Tulevik Viljandi | - | Tallinna JK Legion | 1:0 | ||||
| 16. Ronde | 29.05.2021 | Tallinna JK Legion | - | FCI Levadia | 2:3 | |
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| 4. Ronde | 01.07.2021 | Pärnu JK Vaprus | - | Tallinna JK Legion | 1:4 | |
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| 14. Ronde | 04.07.2021 | JK Tammeka | - | Tallinna JK Legion | 0:2 | ||||
| 17. Ronde | 17.07.2021 | FC Kuressaare | - | Tallinna JK Legion | 1:1 | ||||
| 18. Ronde | 01.08.2021 | JK Nõmme Kalju | - | Tallinna JK Legion | 3:1 |
Estland