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| 06/10/2021 | 19:45 | Hamilton Academical | - | Aberdeen FC (R) | 2:0 (1:0) | |
| 08/10/2021 | 19:45 | Kilmarnock FC | - | Queen's Park FC | 3:1 (1:0) | |
| 19:45 | Queen Of The South | - | Partick Thistle | 2:0 (0:0) | ||
| 09/10/2021 | 13:00 | Raith Rovers | - | East Fife FC | 3:1 (2:1) | |
| 13:30 | Montrose FC | - | Greenock Morton FC | 2:4 (0:0, 0:0) pso | ||
| 14:00 | Elgin City | - | Inverness CT | 2:4 (2:2) | ||
| 14:00 | Cove Rangers | - | Albion Rovers | 4:1 (0:0) | ||
| 27/10/2021 | 19:45 | Alloa Athletic | - | Rangers FC (R) | 2:3 (2:2) |
