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| 14.10.2023 | 13:00 | JK Nõmme Kalju | - | Harju JK | 3:1 (1:0) | |
| 18.10.2023 | 18:00 | Läänemaa JK | - | Arukula FC Vigri | 9:1 (4:0) | |
| 18.11.2023 | 13:00 | Viimsi JK | - | JK Narva Trans | 1:0 (0:0) | |
| 24.11.2023 | 17:00 | Paide Linnameeskond | - | JK Tallinna Kalev II | 4:0 | |
| 18:00 | FCI Levadia | - | JK Tammeka | 4:2 (3:1) | ||
| 25.11.2023 | 11:30 | FC Kuressaare | - | FC Flora II | 4:2 (4:1) | |
| 26.11.2023 | 13:30 | JK Tallinna Kalev | - | Nõmme United | 3:1 (0:1) | |
| 03.12.2023 | 11:30 | FC Flora | - | FC Elva | 10:0 (4:0) |
