| 1. Round | 04/08/2023 | Arbroath FC | - | Dundee United | 0:4 | ||||
| 8. Round | 07/10/2023 | Raith Rovers | - | Dundee United | 1:1 | ||||
| 9. Round | 21/10/2023 | Partick Thistle | - | Dundee United | 0:5 | ||||
| 10. Round | 27/10/2023 | Dundee United | - | Arbroath FC | 6:0 | ||||
| 18. Round | 29/12/2023 | Dundee United | - | Partick Thistle | 3:0 | ||||
| 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 | ||||
| 22. Round | 27/01/2024 | Dundee United | - | Dunfermline Athletic | 0:0 | ||||
| 23. Round | 03/02/2024 | Ayr United | - | Dundee United | 1:2 | ||||
| 24. Round | 16/02/2024 | Raith Rovers | - | Dundee United | 2:1 | ||||
| 30. Round | 23/03/2024 | Dundee United | - | Inverness CT | 1:1 | ||||
| 31. Round | 30/03/2024 | Dundee United | - | Raith Rovers | 2:0 | ||||
| 32. Round | 06/04/2024 | Queen's Park FC | - | Dundee United | 0:5 |  |
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| 33. Round | 12/04/2024 | Greenock Morton FC | - | Dundee United | 1:4 |  |
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| 34. Round | 20/04/2024 | Dundee United | - | Ayr United | 1:0 | ||||
| 35. Round | 26/04/2024 | Airdrieonians FC | - | Dundee United | 0:0 | ||||
| 36. Round | 03/05/2024 | Dundee United | - | Partick Thistle | 4:1 |
Scotland