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 | ||||
4. Round | 31/08/2019 | Arbroath FC | - | Dunfermline Athletic | 1:0 | ||||
5. Round | 13/09/2019 | Arbroath FC | - | Partick Thistle | 1:1 | ||||
6. Round | 21/09/2019 | Dundee United | - | Arbroath FC | 2:1 | ||||
7. Round | 28/09/2019 | Arbroath FC | - | Ayr United | 0:3 |