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| 04/10/2014 | 14:30 | Bo'ness United | - | Culter FC | 7:1 (5:1) | |
| 15:00 | Edinburgh City FC | - | Auchinleck Talbot | 2:1 (2:1) | ||
| 15:00 | Nairn County FC | - | Huntly FC | 2:1 (2:0) | ||
| 15:00 | Arbroath FC | - | Montrose FC | 2:2 (2:1) | ||
| 15:00 | East Fife FC | - | Threave Rovers | 7:0 (4:0) | ||
| 15:00 | The Spartans FC | - | East Kilbride FC | 3:3 (1:2) | ||
| 15:00 | Berwick Rangers | - | Formartine United | 2:0 (2:0) | ||
| 15:00 | Brora Rangers FC | - | Banks O’ Dee FC | 5:0 (4:0) | ||
| 15:00 | Cove Rangers | - | Annan Athletic | 1:2 (1:2) | ||
| 15:00 | Elgin City | - | Forres Mechanics FC | 0:0 (0:0) | ||
| 15:00 | Whitehill Welfare | - | East Stirlingshire FC | 0:1 (0:0) | ||
| 15:00 | Inverurie Loco Works | - | Hurlford United | 0:3 (0:2) | ||
| 15:00 | Gretna FC 2008 | - | Queen's Park FC | 0:1 (0:0) | ||
| 15:00 | Turriff United | - | Clyde FC | 0:3 (0:1) | ||
| 15:00 | Linlithgow Rose | - | Dalbeattie Star | 5:1 (1:0) | ||
| 05/10/2014 | 15:00 | University of Stirling FC | - | Albion Rovers | 1:4 (1:2) | |
| decisive matches | ||||||
|---|---|---|---|---|---|---|
| 11/10/2014 | 14:00 | Montrose FC | - | Arbroath FC | 1:3 aet | |
| 14:00 | East Kilbride FC | - | The Spartans FC | 1:5 | ||
| 15:00 | Forres Mechanics FC | - | Elgin City | 1:3 | ||
