| 1. Round | 04/03/2023 | JK Tallinna Kalev | - | JK Nõmme Kalju | 0:0 | ||||
| 3. Round | 15/03/2023 | Harju JK | - | JK Tallinna Kalev | 0:2 |  |
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| 4. Round | 18/03/2023 | JK Tallinna Kalev | - | FC Flora | 0:2 | ||||
| 6. Round | 09/04/2023 | JK Tallinna Kalev | - | FCI Levadia | 0:2 | ||||
| 7. Round | 15/04/2023 | Paide Linnameeskond | - | JK Tallinna Kalev | 0:1 | ||||
| 2. Round | 19/04/2023 | JK Tammeka | - | JK Tallinna Kalev | 1:2 | ||||
| 8. Round | 22/04/2023 | JK Narva Trans | - | JK Tallinna Kalev | 2:1 | |
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| 9. Round | 29/04/2023 | JK Tallinna Kalev | - | FC Kuressaare | 0:3 | ||||
| 10. Round | 02/05/2023 | JK Nõmme Kalju | - | JK Tallinna Kalev | 1:2 | ||||
| 11. Round | 07/05/2023 | JK Tallinna Kalev | - | JK Tammeka | 1:1 | ||||
| 12. Round | 13/05/2023 | Pärnu JK Vaprus | - | JK Tallinna Kalev | 0:2 | ||||
| 13. Round | 20/05/2023 | FC Kuressaare | - | JK Tallinna Kalev | 1:2 | ||||
| 16. Round | 07/06/2023 | JK Tallinna Kalev | - | JK Narva Trans | 0:1 | ||||
| 17. Round | 11/06/2023 | FCI Levadia | - | JK Tallinna Kalev | 2:1 |
Estonia