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| H | Ayr United | - | Cowdenbeath FC | 1:2 (0:2) | ||
| R | Cowdenbeath FC | - | Ayr United | 3:1 (2:1) | ||
| H: 07.05.2014 20:45 | R: 10.05.2014 16:00 | Sieger: Cowdenbeath FC | ||||
| H | Stranraer FC | - | Dunfermline Athletic | 2:1 (1:1) | ||
| R | Dunfermline Athletic | - | Stranraer FC | 3:0 (0:0, 1:0) n.V. | ||
| H: 07.05.2014 20:45 | R: 10.05.2014 16:00 | Sieger: Dunfermline Athletic | ||||
