| 1. Round | 09/03/2019 | FCI Levadia | - | JK Tallinna Kalev | 5:1 | ||||
| 4. Round | 03/04/2019 | JK Narva Trans | - | FCI Levadia | 1:2 | ||||
| 5. Round | 07/04/2019 | JK Tammeka | - | FCI Levadia | 1:2 | ||||
| 8. Round | 28/04/2019 | FCI Levadia | - | FC Flora | 1:2 | ||||
| 11. Round | 17/05/2019 | Tulevik Viljandi | - | FCI Levadia | 0:3 | ||||
| 13. Round | 29/05/2019 | FC Flora | - | FCI Levadia | 1:3 | ||||
| 15. Round | 14/06/2019 | JK Tallinna Kalev | - | FCI Levadia | 1:6 |  |
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| 16. Round | 19/06/2019 | FCI Levadia | - | JK Narva Trans | 2:0 | ||||
| 20. Round | 21/07/2019 | FC Kuressaare | - | FCI Levadia | 0:3 | ||||
| 28. Round | 14/09/2019 | FCI Levadia | - | Tulevik Viljandi | 1:1 | ||||
| 29. Round | 18/09/2019 | FC Flora | - | FCI Levadia | 2:1 | ||||
| 30. Round | 21/09/2019 | FCI Levadia | - | JK Narva Trans | 1:0 | ||||
| 31. Round | 28/09/2019 | JK Tallinna Kalev | - | FCI Levadia | 0:1 | ||||
| 32. Round | 06/10/2019 | FCI Levadia | - | JK Tammeka | 1:1 | ||||
| 34. Round | 26/10/2019 | Maardu Linnameeskond | - | FCI Levadia | 1:4 | ||||
| 36. Round | 09/11/2019 | Paide Linnameeskond | - | FCI Levadia | 3:1 |
Estonia