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| 31/08/2021 | 19:45 | Hamilton Academical | - | Heart of Midlothian (R) | 3:2 (1:0) | |
| 03/09/2021 | 19:45 | Airdrieonians FC | - | Queen's Park FC | 4:5 (0:0, 1:1) pso | |
| 04/09/2021 | Elgin City | - | Dunfermline Athletic | 3:0 dec. | ||
| 13:00 | Stranraer FC | - | Partick Thistle | 0:2 (0:1) | ||
| 13:30 | Montrose FC | - | Stirling Albion FC | 1:0 (1:0) | ||
| 13:30 | Albion Rovers | - | St. Mirren FC (R) | 6:0 (3:0) | ||
| 15:00 | Aberdeen FC (R) | - | Arbroath FC | 4:1 (0:0, 1:1) pso | ||
| 15:00 | Cove Rangers | - | Stenhousemuir FC | 4:2 (0:0, 0:0) pso | ||
| 15:00 | Cowdenbeath FC | - | Alloa Athletic | 0:2 (0:1) | ||
| 15:00 | Raith Rovers | - | Forfar Athletic | 1:0 (1:0) | ||
| 15:00 | Inverness CT | - | Buckie Thistle | 4:0 (1:0) | ||
| 15:00 | Peterhead FC | - | East Fife FC | 0:1 (0:1) | ||
| 15:00 | Celtic FC (R) | - | Greenock Morton FC | 1:3 (1:2) | ||
| 15:00 | Kilmarnock FC | - | Falkirk FC | 3:1 (1:1) | ||
| 05/09/2021 | 14:00 | Queen Of The South | - | Broomhill FC | 3:0 (1:0) | |
| 14/09/2021 | 19:30 | Rangers FC (R) | - | Ayr United | 3:0 dec. |
