| 2. Round | 14/03/2009 | JK Tallinna Kalev | - | JK Nõmme Kalju | 1:2 |  |
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| 17. Round | 20/06/2009 | JK Nõmme Kalju | - | JK Tallinna Kalev | 2:1 | |
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| 13. Round | 01/08/2009 | FC Levadia | - | JK Nõmme Kalju | 3:1 |  |
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| 25. Round | 22/08/2009 | JK Nõmme Kalju | - | Tulevik Viljandi | 1:1 | |
Estonia