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| 06/10/2009 | 16:45 | JK Nõmme Kalju | - | JK Tallinna Kalev | 3:1 | |
| 07/10/2009 | 14:00 | Lootus Kohtla-Järve | - | FC Atletik | 6:0 | |
| 08/10/2009 | 14:00 | Türi Ganvix JK | - | Võru JK | 4:2 | |
| 10/10/2009 | 10:00 | JK Sillamäe Kalev | - | JK Piraaja Tallinn | 3:0 | |
| 28/10/2009 | 16:00 | FC Flora II | - | Warrior Valga | 0:1 | |
| 16:45 | JK Tammeka | - | Nõmme United | 4:0 | ||
| 14/11/2009 | 11:00 | JK Narva Trans | - | FC Levadia | 0:3 | |
| 21/11/2009 | 11:00 | FC Kuressaare | - | FC Flora | 0:4 |
