1. Round | 03/08/2019 | Arbroath FC | - | Queen Of The South | 0:0 | ||||
2. Round | 10/08/2019 | Inverness CT | - | Arbroath FC | 2:1 | ||||
3. Round | 24/08/2019 | Alloa Athletic | - | Arbroath FC | 0:1 | ||||
5. Round | 13/09/2019 | Arbroath FC | - | Partick Thistle | 1:1 | ||||
6. Round | 21/09/2019 | Dundee United | - | Arbroath FC | 2:1 | ||||
8. Round | 05/10/2019 | Dundee FC | - | Arbroath FC | 2:0 | ||||
9. Round | 19/10/2019 | Arbroath FC | - | Greenock Morton FC | 1:0 | ||||
11. Round | 29/10/2019 | Dunfermline Athletic | - | Arbroath FC | 2:0 | ||||
13. Round | 09/11/2019 | Arbroath FC | - | Inverness CT | 3:0 | ||||
14. Round | 16/11/2019 | Greenock Morton FC | - | Arbroath FC | 1:0 | ||||
15. Round | 10/12/2019 | Ayr United | - | Arbroath FC | 1:1 | ||||
18. Round | 21/12/2019 | Queen Of The South | - | Arbroath FC | 2:0 |