1. Round | 07/03/2009 | FC Levadia | - | FC Kuressaare | 3:0 | ||||
3. Round | 17/03/2009 | FC Levadia | - | JK Tallinna Kalev | 4:1 | ||||
4. Round | 21/03/2009 | Tulevik Viljandi | - | FC Levadia | 0:7 | ||||
5. Round | 04/04/2009 | FC Levadia | - | JK Tammeka | 8:0 | ||||
7. Round | 18/04/2009 | FC Levadia | - | JK Sillamäe Kalev | 3:1 | ||||
8. Round | 25/04/2009 | FC Levadia | - | JK Narva Trans | 2:0 | ||||
9. Round | 02/05/2009 | Paide Linnameeskond | - | FC Levadia | 0:3 | ||||
10. Round | 09/05/2009 | FC Levadia | - | Paide Linnameeskond | 2:0 | ||||
11. Round | 16/05/2009 | JK Narva Trans | - | FC Levadia | 0:3 | ||||
16. Round | 16/06/2009 | JK Tallinna Kalev | - | FC Levadia | 2:2 | ||||
17. Round | 20/06/2009 | FC Levadia | - | FC Flora | 3:2 | ||||
18. Round | 07/07/2009 | FC Kuressaare | - | FC Levadia | 1:7 | ||||
19. Round | 11/07/2009 | Paide Linnameeskond | - | FC Levadia | 1:5 |