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| 18/06/2023 | 18:30 | FC TransferWise | - | Tallinna Wolves | 1:0 (0:0) | |
| 21/06/2023 | 16:00 | Zenit Tallinn | - | FC Hiiumaa | 3:1 (0:0) | |
| 17:00 | Tabasalu Ulasabat CF | - | FC Flora | 4:0 (3:0) | ||
| 18:00 | Kristiine JK | - | FC Kohvile | 2:3 (0:2, 2:2) aet | ||
| 18:00 | FA Tartu Kalev | - | FC Sssolutions | 9:0 (5:0) | ||
| 22/06/2023 | 15:00 | JK Tallinna Kalev | - | Vana Hea Puur | 20:0 (7:0) | |
| 17:00 | Viimsi JK | - | Paide Linnameeskond III | 4:0 (2:0) | ||
| 17:30 | Põhja-Tallinna JK Volta | - | Rumori Calcio | 2:4 (0:2) | ||
| 18:00 | JK Tallinna Kalev Juunior | - | Tallinna JK Legion | 0:10 (0:6) | ||
| 02/07/2023 | 12:00 | Keila JK | - | JK Jalgpallihaigla | 11:0 (6:0) | |
| 12/07/2023 | 17:00 | Jõgeva Wolves | - | FC Kuressaare | 0:8 (0:5) | |
| 14/07/2023 | 18:00 | FC Drakon | - | Nõmme United | 0:12 (0:6) |
