| 15. Round | 15/06/2019 | JK Nõmme Kalju | - | JK Narva Trans | 3:2 | ||||
| 17. Round | 22/06/2019 | JK Nõmme Kalju | - | Tulevik Viljandi | 2:1 |  |
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| 18. Round | 28/06/2019 | JK Tammeka | - | JK Nõmme Kalju | 0:0 | ||||
| 19. Round | 05/07/2019 | JK Narva Trans | - | JK Nõmme Kalju | 1:1 | ||||
| 20. Round | 19/07/2019 | JK Nõmme Kalju | - | Paide Linnameeskond | 1:1 | ||||
| 24. Round | 18/08/2019 | JK Nõmme Kalju | - | Tulevik Viljandi | 2:2 | ||||
| 25. Round | 24/08/2019 | JK Nõmme Kalju | - | FCI Levadia | 2:1 | ||||
| 26. Round | 28/08/2019 | FC Flora | - | JK Nõmme Kalju | 1:1 | ||||
| 28. Round | 14/09/2019 | JK Nõmme Kalju | - | JK Narva Trans | 2:2 |  |
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| 29. Round | 17/09/2019 | Tulevik Viljandi | - | JK Nõmme Kalju | 0:3 | |
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| 30. Round | 21/09/2019 | JK Nõmme Kalju | - | JK Tallinna Kalev | 6:0 | |
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| 21. Round | 24/09/2019 | JK Tallinna Kalev | - | JK Nõmme Kalju | 2:3 | ||||
| 31. Round | 28/09/2019 | JK Nõmme Kalju | - | Maardu Linnameeskond | 4:0 | |
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| 23. Round | 01/10/2019 | Maardu Linnameeskond | - | JK Nõmme Kalju | 1:4 | ||||
| 33. Round | 20/10/2019 | JK Nõmme Kalju | - | FC Flora | 2:1 | ||||
| 34. Round | 28/10/2019 | FC Kuressaare | - | JK Nõmme Kalju | 0:3 | ||||
| 36. Round | 09/11/2019 | JK Nõmme Kalju | - | JK Tammeka | 2:3 |
Estonia