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| 10/08/2021 | Stranraer FC | - | Motherwell FC (R) | 3:0 dec. | ||
| 19:30 | Fraserburgh FC | - | Cowdenbeath FC | 0:1 (0:0) | ||
| 19:30 | Stenhousemuir FC | - | Dundee United (R) | 3:0 (2:0) | ||
| 19:45 | East Fife FC | - | St. Johnstone FC (R) | 1:0 (1:0) | ||
| 19:45 | Hibernian FC (R) | - | Elgin City | 1:2 (0:1) | ||
| 19:45 | Brora Rangers FC | - | Aberdeen FC (R) | 0:1 (0:0) | ||
| 19:45 | Forfar Athletic | - | Formartine United | 1:0 (1:0) | ||
| 19:45 | Ross County FC (R) | - | Stirling Albion FC | 0:3 dec. | ||
| 19:45 | Livingston FC (R) | - | Albion Rovers | 0:3 dec. | ||
| 19:45 | Queen's Park FC | - | Bonnyrigg Rose Athletic | 5:4 (0:0, 1:1) pso | ||
| 19:45 | St. Mirren FC (R) | - | Kelty Hearts | 3:0 (0:0, 1:1) pso | ||
| 11/08/2021 | 19:30 | Falkirk FC | - | East Kilbride FC | 3:0 (1:0) | |
| 19:45 | Dundee FC (R) | - | Peterhead FC | 1:2 (1:1) | ||
| 19:45 | Dumbarton FC | - | Rangers FC (R) | 2:3 (0:2) | ||
| 19:45 | Celtic FC (R) | - | Annan Athletic | 2:0 (1:0) | ||
| 19:45 | Broomhill FC | - | Clyde FC | 1:0 (1:0) | ||
| 20:00 | Brechin City FC | - | Buckie Thistle | 1:3 (0:1) | ||
| 17/08/2021 | 19:45 | Edinburgh City FC | - | Heart of Midlothian (R) | 0:1 (0:1) |
