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| 02/08/2016 | 19:30 | Ross County FC (R) | - | Brora Rangers FC | 2:3 (0:1, 2:2) aet | |
| 19:30 | Clyde FC | - | Partick Thistle (R) | 0:5 (0:0) | ||
| 19:45 | Inverness CT (R) | - | Arbroath FC | 0:3 (0:2) | ||
| 19:45 | Cove Rangers | - | Dundee FC (R) | 2:1 (0:1) | ||
| 19:45 | Formartine United | - | Aberdeen FC (R) | 2:5 (0:1) | ||
| 19:45 | East Stirlingshire FC | - | Montrose FC | 0:3 (0:1) | ||
| 19:45 | Stirling Albion FC | - | Heart of Midlothian (R) | 2:3 (2:0) | ||
| 19:45 | St. Johnstone FC (R) | - | Turriff United | 1:2 (1:0) | ||
| 19:45 | Celtic FC (R) | - | Annan Athletic | 5:1 (3:1) | ||
| 19:45 | Berwick Rangers | - | The Spartans FC | 0:3 (0:2) | ||
| 19:45 | Queen's Park FC | - | Kilmarnock FC (R) | 5:2 (3:2) | ||
| 19:45 | Motherwell FC (R) | - | Edinburgh City FC | 2:1 (1:0) | ||
| 03/08/2016 | 20:00 | Cumbernauld Colts | - | Hamilton Academical (R) | 0:3 (0:1) | |
| 10/08/2016 | 19:30 | Rangers FC (R) | - | University of Stirling FC | 4:0 (4:0) |
