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| 06.08.2019 | 20:30 | Fraserburgh FC | - | Ross County FC (R) | 2:3 (1:1) | |
| 20:45 | Hibernian FC (R) | - | Elgin City | 3:4 (2:3) | ||
| 20:45 | Brora Rangers FC | - | Aberdeen FC (R) | 6:0 (1:0) | ||
| 20:45 | Livingston FC (R) | - | Formartine United | 1:3 (0:2) | ||
| 20:45 | Albion Rovers | - | Heart of Midlothian (R) | 1:4 (1:2) | ||
| 20:45 | St. Johnstone FC (R) | - | Cove Rangers | 1:4 (1:1) | ||
| 20:45 | Kelty Hearts | - | Kilmarnock FC (R) | 4:0 (2:0) | ||
| 20:45 | Berwick Rangers | - | Rangers FC (R) | 1:2 (0:2) | ||
| 20:45 | St. Mirren FC (R) | - | East Kilbride FC | 1:0 (1:0) | ||
| 20:45 | Queen's Park FC | - | Celtic FC (R) | 3:4 (1:2, 2:2) i.E. | ||
| 07.08.2019 | 20:45 | Hamilton Academical (R) | - | BSC Glasgow | 4:0 (1:0) | |
| 20:45 | Motherwell FC (R) | - | The Spartans FC | 1:0 (1:0) |
