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| 27/08/2013 | 19:30 | Greenock Morton FC | - | Montrose FC | 4:0 (0:0) | |
| 19:30 | Stranraer FC | - | Ross County FC | 3:2 (0:1) | ||
| 19:45 | Dundee FC | - | Forfar Athletic | 2:1 (0:1, 1:1) aet | ||
| 19:45 | Falkirk FC | - | Dunfermline Athletic | 2:1 (2:1) | ||
| 19:45 | Kilmarnock FC | - | Hamilton Academical | 0:1 (0:1) | ||
| 19:45 | Airdrieonians FC | - | Livingston FC | 0:2 (0:1) | ||
| 19:45 | Partick Thistle | - | Cowdenbeath FC | 3:1 (0:0, 0:0) aet | ||
| 19:45 | Queen Of The South | - | St. Mirren FC | 2:1 (0:0, 0:0) aet | ||
| 19:45 | Raith Rovers | - | Heart of Midlothian | 4:5 (0:0, 1:1, 1:1) pso | ||
| 19:45 | Aberdeen FC | - | Alloa Athletic | 6:5 (0:0, 0:0, 0:0) pso | ||
| 28/08/2013 | 19:45 | Dumbarton FC | - | Dundee United | 2:3 (1:0) |
