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 Livingston
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