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1/16-finals
1/8-finals
Quarter-finals
Semi-finals
Final
2009/10
1/16-finals
| 1 | Dundee FC | Bye | |
| 2 | Peterhead | Cowdenbeath | 1 : 2 |
| 3 | Stenhousemuir | Clyde | 2 : 0 |
| 4 | Raith | Stirling | 1 : 2 |
| 5 | Elgin City | Brechin | 3 : 1 |
| 6 | Ayr | Albion Rovers | 0 : 2 |
| 7 | East Stirlingshire | Bye | |
| 8 | Queen's Park | Annan | 0 : 2 |
| 9 | Ross County | Alloa | 3 : 2 |
| 10 | Dumbarton | Morton | 0 : 1 |
| 11 | Dunfermline | Arbroath | 2 : 1 |
| 12 | Livingston | Queen of South | 0 : 1 |
| 13 | Partick Thistle | Airdrieonians | 1 : 0 |
| 14 | East Fife | Forfar Athletic | 0 : 2 |
| 15 | Stranraer | Berwick | 4 : 2 |
| 16 | Montrose | Inverness | 1 : 2 |
1/8-finals
| 1 | Dundee FC | Cowdenbeath | 3 : 0 |
| 2 | Stenhousemuir | Stirling | 1 : 3 |
| 3 | Elgin City | Albion Rovers | 3 : 0 |
| 4 | East Stirlingshire | Annan | 0 : 1 |
| 5 | Ross County | Morton | 2 : 1 |
| 6 | Dunfermline | Queen of South | 1 : 2 |
| 7 | Partick Thistle | Forfar Athletic | 6 : 1 |
| 8 | Stranraer | Inverness | 0 : 3 |
Quarter-finals
| 1 | Dundee FC | Stirling | 2 : 1 |
| 2 | Elgin City | Annan | 2 : 4 |
| 3 | Ross County | Queen of South | 2 : 0 |
| 4 | Partick Thistle | Inverness | 1 : 2 |
Semi-finals
| 1 | Dundee FC | Annan | 3 : 0 |
| 2 | Ross County | Inverness | 0 : 1 |
Final
| 1 | Dundee FC | Inverness | 3 : 2 |
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