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| 25/07/2014 | 19:45 | Queen's Park FC | - | Berwick Rangers | 3:4 (1:1, 1:1, 1:1) pso | |
| 26/07/2014 | 15:00 | Arbroath FC | - | Alloa Athletic | 1:4 (0:1) | |
| 15:00 | East Fife FC | - | Forfar Athletic | 2:1 (2:0) | ||
| 15:00 | Montrose FC | - | Peterhead FC | 0:3 (0:3) | ||
| 15:00 | Elgin City | - | Stirling Albion FC | 0:3 (0:0) | ||
| 15:00 | Cowdenbeath FC | - | Brechin City FC | 1:3 (1:0, 1:1) aet | ||
| 15:00 | East Stirlingshire FC | - | Falkirk FC | 1:7 (0:1) | ||
| 15:00 | Brora Rangers FC | - | Stenhousemuir FC | 3:1 (1:0, 1:1) aet | ||
| 15:00 | Stranraer FC | - | Dumbarton FC | 3:2 (0:2) | ||
| 15:00 | Heart of Midlothian | - | Annan Athletic | 3:1 (3:0) | ||
| 15:00 | Airdrieonians FC | - | Albion Rovers | 2:4 (1:1, 2:2, 2:2) pso | ||
| 15:00 | Queen Of The South | - | Livingston FC | 3:4 (1:0, 2:2) aet | ||
| 15:00 | Greenock Morton FC | - | The Spartans FC | 1:0 (1:0) | ||
| 15:00 | Clyde FC | - | Ayr United | 2:0 (2:0) | ||
| 05/08/2014 | 19:35 | Rangers FC | - | Hibernian FC | 2:1 (1:0, 1:1) aet | |
| 19:45 | Dunfermline Athletic | - | Raith Rovers | 1:0 (0:0) |
