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1/32-finals
1/16-finals
1/8-finals
Quarter-finals
Semi-finals
Final
2013/14
1/32-finals
| 1 | Raith | Bye | |
| 2 | Bye | Stirling | |
| 3 | Cowdenbeath | Bye | |
| 4 | Bye | Dunfermline | |
| 5 | Ayr | Bye | |
| 6 | Bye | Queen's Park | |
| 7 | Clyde | Bye | |
| 8 | Bye | Falkirk | |
| 9 | Formartine Utd | Bye | |
| 10 | Bye | East Stirlingshire | |
| 11 | Montrose | Bye | |
| 12 | Bye | Elgin City | |
| 13 | Stranraer | Bye | |
| 14 | Bye | Dumbarton | |
| 15 | Morton | Bye | |
| 16 | Bye | Annan | |
| 17 | Stenhousemuir | Bye | |
| 18 | Bye | Arbroath | |
| 19 | Brechin | Bye | |
| 20 | Bye | Peterhead | |
| 21 | Forfar Athletic | Bye | |
| 22 | Bye | East Fife | |
| 23 | Alloa | Bye | |
| 24 | Bye | Dundee FC | |
| 25 | Queen of South | Bye | |
| 26 | Threave Rovers | Spartans | 1 : 0, 2 : 4 |
| 27 | Hamilton | Bye | |
| 28 | Bye | Airdrieonians | |
| 29 | Berwick | Bye | |
| 30 | Bye | Livingston | |
| 31 | Albion Rovers | Bye | |
| 32 | Bye | Rangers |
1/16-finals
| 1 | Raith | Stirling | 2 : 1 |
| 2 | Cowdenbeath | Dunfermline | 1 : 3 |
| 3 | Ayr | Queen's Park | 2 : 1 |
| 4 | Clyde | Falkirk | 1 : 2 |
| 5 | Formartine Utd | East Stirlingshire | 2 : 0 |
| 6 | Montrose | Elgin City | 0 : 2 |
| 7 | Stranraer | Dumbarton | 4 : 2 |
| 8 | Morton | Annan | 0 : 1 |
| 9 | Stenhousemuir | Arbroath | 5 : 4 |
| 10 | Brechin | Peterhead | 1 : 2 |
| 11 | Forfar Athletic | East Fife | 2 : 1 |
| 12 | Alloa | Dundee FC | 0 : 1 |
| 13 | Queen of South | Spartans | 4 : 0 |
| 14 | Hamilton | Airdrieonians | 1 : 2 |
| 15 | Berwick | Livingston | 3 : 2 |
| 16 | Albion Rovers | Rangers | 0 : 4 |
1/8-finals
| 1 | Raith | Dunfermline | 2 : 0 |
| 2 | Ayr | Falkirk | 1 : 2 |
| 3 | Formartine Utd | Elgin City | 5 : 1 |
| 4 | Stranraer | Annan | 2 : 3 |
| 5 | Stenhousemuir | Peterhead | 3 : 1 |
| 6 | Forfar Athletic | Dundee FC | 1 : 3 |
| 7 | Queen of South | Airdrieonians | 2 : 0 |
| 8 | Berwick | Rangers | 0 : 2 |
Quarter-finals
| 1 | Raith | Falkirk | 1 : 0 |
| 2 | Formartine Utd | Annan | 0 : 4 |
| 3 | Stenhousemuir | Dundee FC | 2 : 1 |
| 4 | Queen of South | Rangers | 0 : 3 |
Semi-finals
| 1 | Raith | Annan | 3 : 0 |
| 2 | Stenhousemuir | Rangers | 0 : 1 |
Final
| 1 | Raith | Rangers | 1 : 0 |
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