1. Round | 04/08/2018 | Ross County FC | - | Alloa Athletic | 1:0 | ||||
2. Round | 11/08/2018 | Dunfermline Athletic | - | Ross County FC | 1:3 | ||||
3. Round | 25/08/2018 | Greenock Morton FC | - | Ross County FC | 2:1 | ||||
4. Round | 01/09/2018 | Ross County FC | - | Falkirk FC | 2:0 | ||||
5. Round | 15/09/2018 | Queen Of The South | - | Ross County FC | 0:0 | ||||
6. Round | 22/09/2018 | Ross County FC | - | Inverness CT | 0:0 | ||||
7. Round | 29/09/2018 | Dundee United | - | Ross County FC | 1:5 | ||||
8. Round | 06/10/2018 | Partick Thistle | - | Ross County FC | 0:2 | ||||
9. Round | 20/10/2018 | Ross County FC | - | Ayr United | 2:1 | ||||
14. Round | 24/11/2018 | Ross County FC | - | Dunfermline Athletic | 2:1 | ||||
19. Round | 29/12/2018 | Ross County FC | - | Inverness CT | 2:1 | ||||
20. Round | 04/01/2019 | Greenock Morton FC | - | Ross County FC | 1:0 |