2. Round | 06/08/2022 | Raith Rovers | - | Dundee FC | 0:1 | ||||
3. Round | 12/08/2022 | Dundee FC | - | Arbroath FC | 4:2 | ||||
4. Round | 20/08/2022 | Greenock Morton FC | - | Dundee FC | 0:0 | ||||
5. Round | 26/08/2022 | Ayr United | - | Dundee FC | 3:1 | ||||
6. Round | 03/09/2022 | Dundee FC | - | Queen's Park FC | 3:0 | ||||
8. Round | 17/09/2022 | Dundee FC | - | Inverness CT | 2:3 | ||||
9. Round | 01/10/2022 | Hamilton Academical | - | Dundee FC | 0:2 | ||||
7. Round | 04/10/2022 | Cove Rangers | - | Dundee FC | 3:1 |