22nd November 2009
| Final | Dundee | 3-2 | Inverness Caledonian Thistle |
4th October 2009
| Semi Final | Inverness Caledonian Thistle | 1-0 | Ross County |
| Semi Final | Dundee | 3-0 | Annan Athletic |
6th September 2009
| Quarter Final | Stirling Albion | 1-2 | Dundee |
| Quarter Final | Annan Athletic | 4-2 | Elgin City |
| Quarter Final | Partick Thistle | 1-1 | Inverness Caledonian Thistle |
| Quarter Final | Ross County | 2-0 | Queen of the South |
18th August 2009
| 2nd Round | Elgin City | 3-0 | Albion Rovers |
| 2nd Round | Cowdenbeath | 0-3 | Dundee |
| 2nd Round | Annan Athletic | 1-0 |
| 2nd Round | Ross County | 2-1 | Greenock Morton |
| 2nd Round | Forfar Athletic | 1-6 | Partick Thistle |
| 2nd Round | Dunfermline Athletic | 1-2 | Queen of the South |
| 2nd Round | Stirling Albion | 3-1 | Stenhousemuir |
| 2nd Round | Inverness Caledonian Thistle | 3-0 | Stranraer |
26th July 2009
| 1st Round South & West Region | Dumbarton | 0-1 | Greenock Morton |
25th July 2009
| 1st Round South & West Region | Ayr United | 0-2 | Albion Rovers |
| 1st Round North & East Region | Ross County | 3-2 | Alloa Athletic |
| 1st Round North & East Region | Dunfermline Athletic | 2-1 | Arbroath |
| 1st Round South & West Region | Stranraer | 4-2 |
| 1st Round North & East Region | Elgin City | 3-1 | Brechin City |
| 1st Round South & West Region | Stenhousemuir | 2-0 | Clyde |
| 1st Round North & East Region | Peterhead | 1-2 | Cowdenbeath |
| 1st Round North & East Region | East Fife | 0-2 | Forfar Athletic |
| 1st Round South & West Region | Queen of the South | 1-0 |
| 1st Round North & East Region | Inverness Caledonian Thistle | 1-1 | Montrose |
| 1st Round South & West Region | Airdrie United | 0-1 | Partick Thistle |
| 1st Round South & West Region | Annan Athletic | 2-0 | Queen's Park |
| 1st Round North & East Region | Stirling Albion | 2-1 | Raith Rovers |