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 | ||||
33. Round | 20/10/2019 | JK Tammeka | - | Tulevik Viljandi | 1:3 | ||||
34. Round | 26/10/2019 | Tulevik Viljandi | - | JK Narva Trans | 0:2 | ||||
35. Round | 03/11/2019 | Tulevik Viljandi | - | Maardu Linnameeskond | 2:1 | ||||
36. Round | 09/11/2019 | JK Tallinna Kalev | - | Tulevik Viljandi | 3:0 |