1. Round | 04/08/2023 | Arbroath FC | - | Dundee United | 0:4 | ||||
2. Round | 12/08/2023 | Dundee United | - | Dunfermline Athletic | 1:1 | ||||
3. Round | 26/08/2023 | Ayr United | - | Dundee United | 0:3 | ||||
4. Round | 02/09/2023 | Dundee United | - | Airdrieonians FC | 2:0 | ||||
5. Round | 16/09/2023 | Dundee United | - | Greenock Morton FC | 1:1 | ||||
6. Round | 23/09/2023 | Inverness CT | - | Dundee United | 0:1 | ||||
7. Round | 30/09/2023 | Dundee United | - | Queen's Park FC | 4:1 | ||||
8. Round | 07/10/2023 | Raith Rovers | - | Dundee United | 1:1 | ||||
10. Round | 27/10/2023 | Dundee United | - | Arbroath FC | 6:0 | ||||
11. Round | 31/10/2023 | Airdrieonians FC | - | Dundee United | 0:2 | ||||
12. Round | 04/11/2023 | Dundee United | - | Inverness CT | 1:1 | ||||
13. Round | 10/11/2023 | Dunfermline Athletic | - | Dundee United | 1:2 | ||||
15. Round | 09/12/2023 | Dundee United | - | Ayr United | 1:0 | ||||
17. Round | 22/12/2023 | Queen's Park FC | - | Dundee United | 0:0 | ||||
19. Round | 02/01/2024 | Arbroath FC | - | Dundee United | 0:3 | ||||
20. Round | 06/01/2024 | Dundee United | - | Greenock Morton FC | 2:3 | ||||
21. Round | 12/01/2024 | Inverness CT | - | Dundee United | 0:1 |