| 22. Round | 05/08/2023 | JK Tallinna Kalev | - | JK Tammeka | 1:1 | ||||
| 23. Round | 12/08/2023 | Paide Linnameeskond | - | JK Tallinna Kalev | 1:1 | ||||
| 24. Round | 20/08/2023 | JK Tallinna Kalev | - | FC Flora | 1:1 |  |
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| 25. Round | 26/08/2023 | FCI Levadia | - | JK Tallinna Kalev | 1:1 | ||||
| 26. Round | 01/09/2023 | JK Narva Trans | - | JK Tallinna Kalev | 2:1 | ||||
| 27. Round | 16/09/2023 | JK Tallinna Kalev | - | Harju JK | 2:1 | ||||
| 28. Round | 22/09/2023 | FC Flora | - | JK Tallinna Kalev | 1:0 | |
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| 29. Round | 27/09/2023 | JK Tallinna Kalev | - | Paide Linnameeskond | 2:1 | ||||
| 30. Round | 01/10/2023 | FC Kuressaare | - | JK Tallinna Kalev | 1:1 | ||||
| 31. Round | 07/10/2023 | JK Tallinna Kalev | - | FCI Levadia | 1:2 | ||||
| 32. Round | 21/10/2023 | JK Tallinna Kalev | - | Pärnu JK Vaprus | 1:0 | |
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| 33. Round | 27/10/2023 | JK Tammeka | - | JK Tallinna Kalev | 2:7 |  |
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| 35. Round | 05/11/2023 | JK Tallinna Kalev | - | JK Nõmme Kalju | 1:1 | ||||
| 36. Round | 11/11/2023 | JK Tallinna Kalev | - | JK Narva Trans | 5:0 | |
Estonia