| 1. Round | 03/03/2023 | FC Flora | - | Harju JK | 4:0 | ||||
| 2. Round | 07/03/2023 | FC Kuressaare | - | Harju JK | 1:1 |  |
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| 3. Round | 15/03/2023 | Harju JK | - | JK Tallinna Kalev | 0:2 | |
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| 4. Round | 19/03/2023 | Harju JK | - | JK Nõmme Kalju | 1:2 | ||||
| 5. Round | 01/04/2023 | Paide Linnameeskond | - | Harju JK | 1:0 | ||||
| 6. Round | 08/04/2023 | Harju JK | - | JK Narva Trans | 1:2 | ||||
| 7. Round | 15/04/2023 | FCI Levadia | - | Harju JK | 6:1 | ||||
| 8. Round | 23/04/2023 | Harju JK | - | JK Tammeka | 2:3 | ||||
| 9. Round | 28/04/2023 | Harju JK | - | Pärnu JK Vaprus | 1:2 | ||||
| 10. Round | 02/05/2023 | JK Narva Trans | - | Harju JK | 2:0 | ||||
| 12. Round | 12/05/2023 | JK Nõmme Kalju | - | Harju JK | 1:1 | ||||
| 13. Round | 19/05/2023 | Harju JK | - | FC Flora | 0:1 | ||||
| 14. Round | 23/05/2023 | Harju JK | - | FC Kuressaare | 1:1 | |
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| 15. Round | 28/05/2023 | Pärnu JK Vaprus | - | Harju JK | 0:1 | |
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| 17. Round | 11/06/2023 | Harju JK | - | Paide Linnameeskond | 0:1 | ||||
| 21. Round | 22/07/2023 | JK Nõmme Kalju | - | Harju JK | 1:0 | ||||
| 22. Round | 06/08/2023 | Harju JK | - | Paide Linnameeskond | 0:1 | ||||
| 31. Round | 08/10/2023 | Paide Linnameeskond | - | Harju JK | 4:0 | ||||
| 32. Round | 22/10/2023 | Harju JK | - | FC Flora | 2:3 |
Estonia