| 21. Round | 30/07/2016 | JK Sillamäe Kalev | - | JK Tammeka | 5:1 | ||||
| 24. Round | 16/08/2016 | Paide Linnameeskond | - | JK Sillamäe Kalev | 1:3 |  |
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| 25. Round | 19/08/2016 | JK Sillamäe Kalev | - | FC Flora | 1:4 | ||||
| 32. Round | 01/10/2016 | JK Nõmme Kalju | - | JK Sillamäe Kalev | 3:1 | ||||
| 33. Round | 15/10/2016 | JK Sillamäe Kalev | - | FC Levadia | 3:2 | |
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| 36. Round | 05/11/2016 | Rakvere JK Tarvas | - | JK Sillamäe Kalev | 0:3 | |
Italy