| 1. Round | 04/08/2023 | Arbroath FC | - | Dundee United | 0:4 | ||||
| 24. Round | 16/02/2024 | Raith Rovers | - | Dundee United | 2:1 | ||||
| 25. Round | 24/02/2024 | Dundee United | - | Queen's Park FC | 3:1 | ||||
| 26. Round | 27/02/2024 | Dundee United | - | Airdrieonians FC | 0:2 | ||||
| 27. Round | 02/03/2024 | Partick Thistle | - | Dundee United | 1:1 | ||||
| 14. Round | 05/03/2024 | Greenock Morton FC | - | Dundee United | 0:1 |  |
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| 28. Round | 09/03/2024 | Dundee United | - | Arbroath FC | 4:0 | ||||
| 29. Round | 15/03/2024 | Dunfermline Athletic | - | Dundee United | 3:1 | ||||
| 30. Round | 23/03/2024 | Dundee United | - | Inverness CT | 1:1 | ||||
| 31. Round | 30/03/2024 | Dundee United | - | Raith Rovers | 2:0 | |
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| 32. Round | 06/04/2024 | Queen's Park FC | - | Dundee United | 0:5 | ||||
| 33. Round | 12/04/2024 | Greenock Morton FC | - | Dundee United | 1:4 | ||||
| 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