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| 05/08/2014 | 17:00 | Jõhvi FC Lokomotiv | - | JK Tallinna Kalev III | 3:1 | |
| 06/08/2014 | 17:00 | Metropool Pärnu | - | FC Ararat TTÜ | 1:3 pso | |
| 17:00 | SK Tääksi | - | Kiviõli FC Irbis | 3:7 | ||
| 18:45 | FC Infonet II | - | Rakvere JK Tarvas | 2:1 | ||
| 12/08/2014 | 16:00 | Võru JK | - | FC Infonet | 0:11 | |
| 16:00 | FC Flora II | - | JK Tammeka | 3:1 | ||
| 18:30 | FC Flora | - | FC Kose | 13:0 | ||
| 14/08/2014 | 17:00 | FC Tartu | - | JK Retro | 2:5 | |
| 17/08/2014 | 18:45 | FC Flora III | - | Viimsi FC Igiliikur | 2:3 | |
| 19/08/2014 | 18:30 | Tallinna FC Charma | - | Tallinna Ülikool | 2:11 | |
| 26/08/2014 | 16:00 | Jõgeva SK Noorus | - | JK Tallinna Kalev | 0:1 | |
| 02/09/2014 | 16:00 | FC Levadia | - | Saue JK Laagri | 0:0 dec. | |
| 17:00 | Keila JK | - | Paide Linnameeskond | 0:6 | ||
| 17:00 | FC Dnipro Tallinn | - | JK Sillamäe Kalev | 0:13 | ||
| 03/09/2014 | 16:30 | Maardu FC Starbunker | - | Türi Ganvix JK | 5:1 | |
| 01/10/2014 | 14:00 | JK Nõmme Kalju | - | FC Kuressaare | 4:0 |
