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| 05/09/2018 | 16:00 | Maardu Linnameeskond | - | Läänemaa JK | 4:0 (3:0) | |
| 06/09/2018 | 15:30 | FC Järva-Jaani | - | JK Tammeka | 0:6 (0:1) | |
| 25/09/2018 | 17:00 | FCI Levadia | - | FC Flora | 2:1 (1:1) | |
| 17:00 | JK Narva Trans | - | Jõgeva SK Noorus | 8:0 (3:0) | ||
| 17:00 | Paide Linnameeskond | - | Tallinna JK Legion | 2:1 (0:1) | ||
| 18:00 | Tabasalu JK | - | Zenit Tallinn | 6:1 (1:0) | ||
| 26/09/2018 | 17:00 | JK Nõmme Kalju | - | JK Tallinna Kalev | 3:0 (0:0, 0:0) aet | |
| 17:00 | Viimsi JK II | - | FC Elva | 0:3 (0:0) |
