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| 24/09/2014 | 18:45 | Tallinna Ülikool | - | JK Retro | 4:3 aet | |
| 01/10/2014 | 18:45 | FC Ararat TTÜ | - | FC Infonet II | 0:3 | |
| 11/10/2014 | Paide Linnameeskond | - | Kiviõli FC Irbis | 3:0 dec. | ||
| 11:00 | JK Tallinna Kalev | - | Jõhvi FC Lokomotiv | 0:3 | ||
| 11:00 | Maardu FC Starbunker | - | JK Nõmme Kalju | 0:4 | ||
| 21/10/2014 | 13:00 | JK Sillamäe Kalev | - | FC Infonet | 4:2 pso | |
| 17:00 | FC Flora | - | Saue JK Laagri | 11:0 | ||
| 22/10/2014 | 18:30 | Viimsi FC Igiliikur | - | FC Flora II | 0:9 |
