| 1. Round | 17/10/2020 | Raith Rovers | - | Arbroath FC | 3:0 | ||||
| 2. Round | 23/10/2020 | Arbroath FC | - | Heart of Midlothian | 0:1 | ||||
| 3. Round | 31/10/2020 | Inverness CT | - | Arbroath FC | 3:1 | ||||
| 4. Round | 07/11/2020 | Arbroath FC | - | Queen Of The South | 1:1 | ||||
| 6. Round | 05/12/2020 | Dundee FC | - | Arbroath FC | 1:0 | ||||
| 7. Round | 12/12/2020 | Arbroath FC | - | Alloa Athletic | 0:1 | ||||
| 8. Round | 19/12/2020 | Arbroath FC | - | Ayr United | 2:1 | ||||
| 9. Round | 26/12/2020 | Dunfermline Athletic | - | Arbroath FC | 1:0 | ||||
| 13. Round | 16/01/2021 | Queen Of The South | - | Arbroath FC | 2:2 | ||||
| 14. Round | 22/01/2021 | Arbroath FC | - | Dundee FC | 1:1 |  |
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| 12. Round | 30/01/2021 | Greenock Morton FC | - | Arbroath FC | 0:1 |
Scotland