1. Round | 10/03/2019 | FC Flora | - | Tulevik Viljandi | 2:0 | ||||
2. Round | 16/03/2019 | Tulevik Viljandi | - | JK Tammeka | 0:4 | ||||
3. Round | 31/03/2019 | Tulevik Viljandi | - | FC Kuressaare | 1:2 | ||||
4. Round | 03/04/2019 | JK Tallinna Kalev | - | Tulevik Viljandi | 0:2 | ||||
11. Round | 17/05/2019 | Tulevik Viljandi | - | FCI Levadia | 0:3 | ||||
12. Round | 24/05/2019 | FC Kuressaare | - | Tulevik Viljandi | 1:0 | ||||
13. Round | 28/05/2019 | Tulevik Viljandi | - | JK Narva Trans | 1:1 | ||||
14. Round | 01/06/2019 | JK Tammeka | - | Tulevik Viljandi | 0:1 | ||||
15. Round | 14/06/2019 | Paide Linnameeskond | - | Tulevik Viljandi | 6:0 | ||||
16. Round | 18/06/2019 | Tulevik Viljandi | - | Maardu Linnameeskond | 2:0 | ||||
17. Round | 22/06/2019 | JK Nõmme Kalju | - | Tulevik Viljandi | 2:1 | ||||
18. Round | 30/06/2019 | Tulevik Viljandi | - | JK Tallinna Kalev | 1:2 | ||||
19. Round | 06/07/2019 | Tulevik Viljandi | - | JK Tammeka | 0:1 | ||||
20. Round | 21/07/2019 | JK Narva Trans | - | Tulevik Viljandi | 3:2 | ||||
21. Round | 28/07/2019 | Tulevik Viljandi | - | FCI Levadia | 0:3 | ||||
22. Round | 25/09/2019 | FC Flora | - | Tulevik Viljandi | 3:0 |