| 1. Round | 08/03/2019 | JK Nõmme Kalju | - | Paide Linnameeskond | 0:2 | ||||
| 2. Round | 17/03/2019 | Maardu Linnameeskond | - | JK Nõmme Kalju | 0:5 | ||||
| 3. Round | 30/03/2019 | JK Narva Trans | - | JK Nõmme Kalju | 0:0 |  |
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| 4. Round | 02/04/2019 | JK Nõmme Kalju | - | FC Flora | 0:3 | ||||
| 11. Round | 17/05/2019 | JK Nõmme Kalju | - | FC Kuressaare | 3:2 |  |
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| 12. Round | 21/05/2019 | FCI Levadia | - | JK Nõmme Kalju | 0:0 |
Chile
Paraguay