7. Round | 04/10/2022 | Cove Rangers | - | Dundee FC | 3:1 | ||||
10. Round | 08/10/2022 | Arbroath FC | - | Dundee FC | 1:1 | ||||
11. Round | 15/10/2022 | Dundee FC | - | Ayr United | 2:1 | ||||
13. Round | 28/10/2022 | Queen's Park FC | - | Dundee FC | 2:2 | ||||
15. Round | 12/11/2022 | Dundee FC | - | Raith Rovers | 2:0 | ||||
16. Round | 19/11/2022 | Dundee FC | - | Hamilton Academical | 1:0 | ||||
19. Round | 23/12/2022 | Ayr United | - | Dundee FC | 0:2 | ||||
20. Round | 02/01/2023 | Dundee FC | - | Arbroath FC | 2:4 | ||||
21. Round | 06/01/2023 | Raith Rovers | - | Dundee FC | 1:1 | ||||
23. Round | 28/01/2023 | Dundee FC | - | Queen's Park FC | 3:0 |