| 22. Round | 06/08/2023 | Harju JK | - | Paide Linnameeskond | 0:1 | ||||
| 23. Round | 12/08/2023 | FCI Levadia | - | Harju JK | 1:1 | ||||
| 24. Round | 18/08/2023 | Harju JK | - | JK Narva Trans | 0:2 | ||||
| 25. Round | 25/08/2023 | FC Flora | - | Harju JK | 2:0 | ||||
| 26. Round | 02/09/2023 | Harju JK | - | Pärnu JK Vaprus | 0:4 |
Germany