| 1. Round | 31/07/2021 | Dundee FC | - | St. Mirren FC | 2:2 |  |
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| 2. Round | 08/08/2021 | Celtic FC | - | Dundee FC | 6:0 | ||||
| 3. Round | 22/08/2021 | Dundee FC | - | Hibernian FC | 2:2 | |
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| 4. Round | 28/08/2021 | Motherwell FC | - | Dundee FC | 1:0 | ||||
| 5. Round | 11/09/2021 | Dundee FC | - | Livingston FC | 0:0 | ||||
| 6. Round | 19/09/2021 | Dundee United | - | Dundee FC | 1:0 | ||||
| 7. Round | 25/09/2021 | Dundee FC | - | Rangers FC | 0:1 | ||||
| 8. Round | 02/10/2021 | St. Johnstone FC | - | Dundee FC | 3:1 | ||||
| 10. Round | 23/10/2021 | Heart of Midlothian | - | Dundee FC | 1:1 | |
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| 11. Round | 27/10/2021 | Dundee FC | - | Ross County FC | 0:5 | ||||
| 13. Round | 07/11/2021 | Dundee FC | - | Celtic FC | 2:4 | ||||
| 17. Round | 04/12/2021 | Rangers FC | - | Dundee FC | 3:0 | ||||
| 18. Round | 11/12/2021 | Ross County FC | - | Dundee FC | 3:2 | ||||
| 14. Round | 14/12/2021 | Hibernian FC | - | Dundee FC | 1:0 |
Scotland