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 | ||||
10. Round | 27/10/2018 | Ross County FC | - | Greenock Morton FC | 5:0 | ||||
11. Round | 30/10/2018 | Falkirk FC | - | Ross County FC | 1:1 | ||||
12. Round | 03/11/2018 | Inverness CT | - | Ross County FC | 2:2 | ||||
13. Round | 10/11/2018 | Ross County FC | - | Dundee United | 0:1 | ||||
35. Round | 26/04/2019 | Ross County FC | - | Queen Of The South | 4:0 | ||||
36. Round | 04/05/2019 | Falkirk FC | - | Ross County FC | 3:2 |