| 2. Jornada | 14.03.2009 | FC Flora | - | FC Levadia | 1:3 |  |
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| 4. Jornada | 21.03.2009 | Tulevik Viljandi | - | FC Levadia | 0:7 | |
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| 6. Jornada | 11.04.2009 | JK Nõmme Kalju | - | FC Levadia | 1:2 | |
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| 7. Jornada | 18.04.2009 | FC Levadia | - | JK Sillamäe Kalev | 3:1 | |
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| 15. Jornada | 13.06.2009 | FC Levadia | - | Tulevik Viljandi | 5:0 | |
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| 18. Jornada | 07.07.2009 | FC Kuressaare | - | FC Levadia | 1:7 | |
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| 23. Jornada | 08.08.2009 | FC Levadia | - | JK Tammeka | 6:1 | |
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| 29. Jornada | 26.09.2009 | FC Levadia | - | FC Flora | 1:0 | |
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| 22. Jornada | 29.09.2009 | JK Nõmme Kalju | - | FC Levadia | 1:3 | |
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| 31. Jornada | 17.10.2009 | FC Levadia | - | Tulevik Viljandi | 3:0 | |
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| 14. Jornada | 20.10.2009 | JK Tammeka | - | FC Levadia | 0:2 | |
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| 33. Jornada | 31.10.2009 | JK Nõmme Kalju | - | FC Levadia | 0:5 | |
Estonia