| 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 |  |
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| 7. Round | 30/09/2023 | Dundee United | - | Queen's Park FC | 4:1 | ||||
| 21. Round | 12/01/2024 | Inverness CT | - | Dundee United | 0:1 | ||||
| 22. Round | 27/01/2024 | Dundee United | - | Dunfermline Athletic | 0:0 | ||||
| 25. Round | 24/02/2024 | Dundee United | - | Queen's Park FC | 3:1 | ||||
| 26. Round | 27/02/2024 | Dundee United | - | Airdrieonians FC | 0:2 | ||||
| 28. Round | 09/03/2024 | Dundee United | - | Arbroath FC | 4:0 |
Scotland