| 1. Round | 17/10/2020 | Ayr United | - | Queen Of The South | 2:1 |  |
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| 2. Round | 24/10/2020 | Inverness CT | - | Ayr United | 1:1 | ||||
| 3. Round | 31/10/2020 | Greenock Morton FC | - | Ayr United | 3:2 | ||||
| 4. Round | 07/11/2020 | Ayr United | - | Dunfermline Athletic | 0:0 | ||||
| 5. Round | 21/11/2020 | Ayr United | - | Dundee FC | 2:0 | ||||
| 6. Round | 05/12/2020 | Alloa Athletic | - | Ayr United | 0:2 | ||||
| 7. Round | 11/12/2020 | Ayr United | - | Raith Rovers | 0:0 | |
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| 8. Round | 19/12/2020 | Arbroath FC | - | Ayr United | 2:1 | ||||
| 9. Round | 26/12/2020 | Heart of Midlothian | - | Ayr United | 5:3 | ||||
| 11. Round | 02/01/2021 | Queen Of The South | - | Ayr United | 3:2 | |
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| 24. Round | 10/04/2021 | Ayr United | - | Dunfermline Athletic | 1:1 | ||||
| 25. Round | 17/04/2021 | Arbroath FC | - | Ayr United | 4:0 | ||||
| 26. Round | 24/04/2021 | Ayr United | - | Queen Of The South | 0:0 | |
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| 27. Round | 30/04/2021 | Inverness CT | - | Ayr United | 2:2 |
England