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| 13/08/2019 | 19:30 | Stenhousemuir FC | - | Edinburgh City FC | 2:1 (1:0) | |
| 19:45 | Heart of Midlothian (R) | - | Cowdenbeath FC | 3:1 (0:0) | ||
| 19:45 | Ross County FC (R) | - | Raith Rovers | 2:3 (0:2) | ||
| 19:45 | Brora Rangers FC | - | Cove Rangers | 1:2 (0:0) | ||
| 19:45 | Peterhead FC | - | Formartine United | 6:7 (0:0, 0:0) pso | ||
| 19:45 | East Fife FC | - | Stirling Albion FC | 0:2 (0:1) | ||
| 19:45 | Brechin City FC | - | Elgin City | 4:5 (3:3) | ||
| 19:45 | Montrose FC | - | Forfar Athletic | 2:1 (1:1) | ||
| 19:45 | Clyde FC | - | Motherwell FC (R) | 4:0 (1:0) | ||
| 19:45 | Annan Athletic | - | Kelty Hearts | 5:6 (1:0, 1:1) pso | ||
| 19:45 | Hamilton Academical (R) | - | Airdrieonians FC | 0:1 (0:1) | ||
| 19:45 | Dumbarton FC | - | St. Mirren FC (R) | 0:1 (0:1) | ||
| 19:45 | Falkirk FC | - | Celtic FC (R) | 6:5 (1:1, 1:1) pso | ||
| 19:45 | Stranraer FC | - | Rangers FC (R) | 0:2 (0:0) |
