| 1. Round | 07/03/2020 | JK Tallinna Kalev | - | Paide Linnameeskond | 1:8 |  |
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| 2. Round | 20/05/2020 | JK Tallinna Kalev | - | JK Narva Trans | 1:1 | ||||
| 3. Round | 24/05/2020 | JK Tammeka | - | JK Tallinna Kalev | 0:2 | ||||
| 4. Round | 30/05/2020 | FC Flora | - | JK Tallinna Kalev | 3:0 | ||||
| 5. Round | 02/06/2020 | JK Tallinna Kalev | - | Tallinna JK Legion | 1:0 | ||||
| 6. Round | 06/06/2020 | FCI Levadia | - | JK Tallinna Kalev | 4:0 | ||||
| 7. Round | 14/06/2020 | JK Tallinna Kalev | - | JK Nõmme Kalju | 0:4 | |
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| 8. Round | 17/06/2020 | JK Tallinna Kalev | - | FC Kuressaare | 0:2 | ||||
| 9. Round | 27/06/2020 | Tulevik Viljandi | - | JK Tallinna Kalev | 2:1 | ||||
| 10. Round | 30/06/2020 | Tallinna JK Legion | - | JK Tallinna Kalev | 0:0 |
Estonia