| 1. Round | 09/03/2019 | JK Narva Trans | - | FC Kuressaare | 0:0 | ||||
| 2. Round | 16/03/2019 | JK Tallinna Kalev | - | JK Narva Trans | 0:4 | ||||
| 3. Round | 30/03/2019 | JK Narva Trans | - | JK Nõmme Kalju | 0:0 | ||||
| 4. Round | 03/04/2019 | JK Narva Trans | - | FCI Levadia | 1:2 | ||||
| 5. Round | 06/04/2019 | Paide Linnameeskond | - | JK Narva Trans | 0:0 | ||||
| 6. Round | 13/04/2019 | JK Narva Trans | - | FC Flora | 0:1 | ||||
| 7. Round | 20/04/2019 | JK Tammeka | - | JK Narva Trans | 1:2 |  |
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| 8. Round | 27/04/2019 | Maardu Linnameeskond | - | JK Narva Trans | 0:1 | ||||
| 11. Round | 18/05/2019 | FC Flora | - | JK Narva Trans | 2:2 | ||||
| 12. Round | 22/05/2019 | JK Narva Trans | - | Maardu Linnameeskond | 5:1 | ||||
| 13. Round | 28/05/2019 | Tulevik Viljandi | - | JK Narva Trans | 1:1 | |
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| 14. Round | 31/05/2019 | JK Narva Trans | - | JK Tallinna Kalev | 2:2 | ||||
| 18. Round | 29/06/2019 | FC Kuressaare | - | JK Narva Trans | 1:1 | |
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| 19. Round | 05/07/2019 | JK Narva Trans | - | JK Nõmme Kalju | 1:1 |
Russia