7. Round | 28/09/2019 | Arbroath FC | - | Ayr United | 0:3 | ||||
8. Round | 05/10/2019 | Dundee FC | - | Arbroath FC | 2:0 | ||||
11. Round | 29/10/2019 | Dunfermline Athletic | - | Arbroath FC | 2:0 | ||||
12. Round | 02/11/2019 | Arbroath FC | - | Alloa Athletic | 2:1 | ||||
13. Round | 09/11/2019 | Arbroath FC | - | Inverness CT | 3:0 | ||||
14. Round | 16/11/2019 | Greenock Morton FC | - | Arbroath FC | 1:0 |