|
| Sunday, November 22, 2009 | ||||
| Final | ||||
| Dundee | 3 - 2 | Inverness Caledonian Thistle | Match report | |
| Half-time: 0 - 2 | ||||
| Sunday, October 4, 2009 | ||||
| Semi-Final | ||||
| Dundee | 3 - 0 | Annan Athletic | Match report | |
| Half-time: 1 - 0 | ||||
| Inverness Caledonian Thistle | 1 - 0 | Ross County | Match report | |
| Half-time: 1 - 0 | ||||
| Sunday, September 6, 2009 | ||||
| Quarter Final | ||||
| Annan Athletic | 4 - 2 | Elgin City | Match report | |
| Half-time: 0 - 2 | ||||
| Partick Thistle | 1 - 1 | Inverness Caledonian Thistle | Match reportInverness win 4-3 on penalties | |
|
Half-time: 0 - 1 Full-time: 1 - 1 Extra-time: 1 - 1 |
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| Ross County | 2 - 0 | Queen of the South | Match report | |
| Half-time: 1 - 0 | ||||
| Stirling Albion | 1 - 2 | Dundee | Match report | |
| Half-time: 0 - 2 | ||||
| Tuesday, August 18, 2009 | ||||
| Second Round | ||||
| Annan Athletic | 1 - 0 | East Stirlingshire | Match report | |
| Half-time: 0 - 0 | ||||
| Cowdenbeath | 0 - 3 | Dundee | Match report | |
| Half-time: 0 - 1 | ||||
| Dunfermline Athletic | 1 - 2 | Queen of the South | Match report | |
| Half-time: 0 - 1 | ||||
| Elgin City | 3 - 0 | Albion Rovers | Match report | |
| Half-time: 0 - 0 | ||||
| Forfar Athletic | 1 - 6 | Partick Thistle | Match report | |
| Half-time: 0 - 1 | ||||
| Inverness Caledonian Thistle | 3 - 0 | Stranraer | Match report | |
| Half-time: 3 - 0 | ||||
| Ross County | 2 - 1 | Morton | Match report | |
| Half-time: 0 - 0 | ||||
| Stirling Albion | 3 - 1 | Stenhousemuir | Match report | |
| Half-time: 1 - 0 | ||||
| Sunday, July 26, 2009 | ||||
| First Round South-West | ||||
| Dumbarton | 0 - 1 | Morton | ||
| Half-time: 0 - 1 | ||||
| Saturday, July 25, 2009 | ||||
| First Round North-East | ||||
| Dunfermline Athletic | 2 - 1 | Arbroath | ||
| Half-time: 0 - 0 | ||||
| East Fife | 0 - 2 | Forfar Athletic | ||
| Half-time: 0 - 1 | ||||
| Elgin City | 3 - 1 | Brechin City | ||
| Half-time: 1 - 0 | ||||
| Inverness Caledonian Thistle | 1 - 1 | Montrose | Inverness CT win 5-3 on penalties | |
|
Half-time: 1 - 0 Full-time: 1 - 1 Extra-time: 1 - 1 |
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| Peterhead | 1 - 2 | Cowdenbeath | ||
| Half-time: 1 - 0 | ||||
| Ross County | 3 - 2 | Alloa Athletic | ||
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Half-time: 0 - 1 Full-time: 1 - 1 Extra-time: 3 - 2 |
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| Stirling Albion | 2 - 1 | Raith Rovers | ||
| Half-time: 1 - 0 | ||||
| First Round South-West | ||||
| Airdrie United | 0 - 1 | Partick Thistle | ||
| Half-time: 0 - 0 | ||||
| Annan Athletic | 2 - 0 | Queen's Park | ||
| Half-time: 1 - 0 | ||||
| Ayr United | 0 - 2 | Albion Rovers | ||
| Half-time: 0 - 0 | ||||
| Queen of the South | 1 - 0 | Livingston | ||
| Half-time: 1 - 0 | ||||
| Stenhousemuir | 2 - 0 | Clyde | ||
| Half-time: 0 - 0 | ||||
| Stranraer | 4 - 2 | Berwick Rangers | ||
| Half-time: 2 - 1 | ||||