| 1. Jornada | 04.08.2023 | Arbroath FC | - | Dundee United | 0:4 | ||||
| 2. Jornada | 12.08.2023 | Dundee United | - | Dunfermline Athletic | 1:1 | ||||
| 3. Jornada | 26.08.2023 | Ayr United | - | Dundee United | 0:3 |  |
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| 4. Jornada | 02.09.2023 | Dundee United | - | Airdrieonians FC | 2:0 | ||||
| 5. Jornada | 16.09.2023 | Dundee United | - | Greenock Morton FC | 1:1 | ||||
| 6. Jornada | 23.09.2023 | Inverness CT | - | Dundee United | 0:1 | ||||
| 7. Jornada | 30.09.2023 | Dundee United | - | Queen's Park FC | 4:1 | ||||
| 8. Jornada | 07.10.2023 | Raith Rovers | - | Dundee United | 1:1 | ||||
| 10. Jornada | 27.10.2023 | Dundee United | - | Arbroath FC | 6:0 | ||||
| 11. Jornada | 31.10.2023 | Airdrieonians FC | - | Dundee United | 0:2 | ||||
| 12. Jornada | 04.11.2023 | Dundee United | - | Inverness CT | 1:1 | ||||
| 13. Jornada | 10.11.2023 | Dunfermline Athletic | - | Dundee United | 1:2 | ||||
| 15. Jornada | 09.12.2023 | Dundee United | - | Ayr United | 1:0 | ||||
| 17. Jornada | 22.12.2023 | Queen's Park FC | - | Dundee United | 0:0 | ||||
| 19. Jornada | 02.01.2024 | Arbroath FC | - | Dundee United | 0:3 | ||||
| 20. Jornada | 06.01.2024 | Dundee United | - | Greenock Morton FC | 2:3 | |
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| 21. Jornada | 12.01.2024 | Inverness CT | - | Dundee United | 0:1 |
Escocia