| 1. Round | 01/08/2021 | Aberdeen FC | - | Dundee United | 2:0 |  |
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| 2. Round | 07/08/2021 | Dundee United | - | Rangers FC | 1:0 | |
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| 4. Round | 28/08/2021 | Dundee United | - | Heart of Midlothian | 0:2 | ||||
| 5. Round | 11/09/2021 | St. Mirren FC | - | Dundee United | 0:0 | |
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| 6. Round | 19/09/2021 | Dundee United | - | Dundee FC | 1:0 | |
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| 14. Round | 20/11/2021 | Dundee United | - | Aberdeen FC | 1:0 |  |
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| 17. Round | 05/12/2021 | Dundee United | - | Celtic FC | 0:3 | |
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| 23. Round | 26/01/2022 | Dundee United | - | Ross County FC | 2:1 | ||||
| 24. Round | 29/01/2022 | Celtic FC | - | Dundee United | 1:0 | |
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| 22. Round | 01/02/2022 | Dundee FC | - | Dundee United | 0:0 | ||||
| 25. Round | 05/02/2022 | St. Johnstone FC | - | Dundee United | 0:0 | ||||
| 26. Round | 09/02/2022 | Dundee United | - | Motherwell FC | 2:0 | ||||
| 27. Round | 20/02/2022 | Dundee United | - | Rangers FC | 1:1 | ||||
| 28. Round | 26/02/2022 | Aberdeen FC | - | Dundee United | 1:1 | ||||
| 29. Round | 02/03/2022 | Livingston FC | - | Dundee United | 2:1 | ||||
| 30. Round | 05/03/2022 | Dundee United | - | Heart of Midlothian | 2:2 | |
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| 31. Round | 19/03/2022 | St. Mirren FC | - | Dundee United | 1:2 |
England