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| 16.08.2023 | 17:00 | FA Tartu Kalev | - | FCI Levadia | 2:6 (1:2) | |
| 22.08.2023 | 17:00 | FC Elva | - | JK Tervis Pärnu | 5:2 (0:1) | |
| 18:00 | Nõmme United | - | Eston Villa | 11:1 (5:1) | ||
| 23.08.2023 | 18:00 | JK Narva Trans | - | Zenit Tallinn | 5:0 (2:0) | |
| 19:30 | Tallinna FC Zapoos | - | JK Tallinna Kalev | 1:4 (1:4) | ||
| 29.08.2023 | 18:00 | FC Maksatransport | - | Läänemaa JK | 0:3 (0:1) | |
| 30.08.2023 | 19:00 | Team Helm JK | - | JK Tallinna Kalev II | 3:7 (0:3) | |
| 06.09.2023 | 18:00 | Pärnu JK Poseidon | - | Arukula FC Vigri | 2:3 (0:0, 1:1) n.v. | |
| 09.09.2023 | 11:30 | FC Kuressaare | - | FC Kose | 9:1 (6:0) | |
| 11.09.2023 | 16:30 | JK Nõmme Kalju | - | Tulevik Viljandi | 5:1 (2:1) | |
| 18:00 | Tallinna Olympic | - | Harju JK | 0:8 (0:4) | ||
| 13.09.2023 | 18:00 | FC Flora II | - | Tallinna JK Legion II | 13:0 (5:0) | |
| 20.09.2023 | 18:00 | Tallinna JK Legion | - | JK Tammeka | 1:3 (1:0) | |
| 14.10.2023 | 18:00 | FC Tallinn | - | Viimsi JK | 5:6 (0:1, 1:1, 1:1) d.p. | |
| 18.10.2023 | 18:00 | Tabasalu JK | - | Paide Linnameeskond | 1:3 (0:0, 1:1) n.v. | |
| 25.11.2023 | 18:00 | FC Flora | - | Pärnu JK Vaprus | 1:0 (1:0) |
