15th May 2010
| Final | Dundee United | 3-0 | Ross County |
11th April 2010
| Semi Final | Dundee United | 2-0 | Raith Rovers |
10th April 2010
| Semi Final | Celtic | 0-2 | Ross County |
24th March 2010
| Quarter Final Replay | Dundee United | 1-0 | Rangers |
23rd March 2010
| Quarter Final Replay | Ross County | 2-1 | Hibernian |
14th March 2010
| Quarter Final | Rangers | 3-3 | Dundee United |
13th March 2010
| Quarter Final | Dundee | 1-2 | Raith Rovers |
| Quarter Final | Hibernian | 2-2 | Ross County |
| Quarter Final | Kilmarnock | 0-3 | Celtic |
17th February 2010
| 5th Round Replay | Rangers | 1-0 | St. Mirren |
16th February 2010
| 5th Round Replay | Aberdeen | 0-1 | Raith Rovers |
7th February 2010
| 5th Round | Dunfermline Athletic | 2-4 | Celtic |
6th February 2010
| 5th Round | Ross County | 9-0 | Stirling Albion |
| 5th Round | Dundee | 2-1 | Ayr United |
| 5th Round | St. Mirren | 0-0 | Rangers |
| 5th Round | St. Johnstone | 0-1 | Dundee United |
| 5th Round | Kilmarnock | 3-0 | Inverness Caledonian Thistle |
| 5th Round | Raith Rovers | 1-1 | Aberdeen |
| 5th Round | Hibernian | 5-1 | Montrose |
26th January 2010
| 4th Round Replay | Stenhousemuir | 1-2 | Dunfermline Athletic |
25th January 2010
| 4th Round | Raith Rovers | 1-1 | Airdrie United |
20th January 2010
| 4th Round Replay | Stirling Albion | 3-1 | Albion Rovers |
| 4th Round | Livingston | 0-1 | Dundee |
19th January 2010
| 4th Round Replay | Rangers | 2-0 |
| 4th Round | Greenock Morton | 0-1 | Celtic |
18th January 2010
| 4th Round | Ayr United | 1-0 | Brechin City |
| 4th Round | Albion Rovers | 0-0 | Stirling Albion |
| 4th Round | Ross County | 4-0 |
| 4th Round | Kilmarnock | 1-0 | Falkirk |
| 4th Round | Inverness Caledonian Thistle | 2-0 | Motherwell |
| 4th Round | Forfar Athletic | 0-3 | St. Johnstone |
| 4th Round | Edinburgh City | 1-3 | Montrose |
10th January 2010
| 4th Round | 3-3 | Rangers |
9th January 2010
| 4th Round | Aberdeen | 2-0 | Heart of Midlothian |
| 4th Round | St. Mirren | 3-1 | Alloa Athletic |
| 4th Round | Partick Thistle | 0-2 | Dundee United |
| 4th Round | Hibernian | 3-0 |
| 4th Round | Dunfermline Athletic | 7-1 | Stenhousemuir |
14th December 2009
| 3rd Round Replay | Livingston | 7-1 | Clyde |
9th December 2009
| 3rd Round | Clyde | 1-1 | Livingston |
8th December 2009
| 3rd Round Replay | Alloa Athletic | 1-0 | Cowdenbeath |
| 3rd Round Replay | Brechin City | 4-2 |
5th December 2009
| 3rd Round Replay | Dumbarton | 0-1 | Greenock Morton |
| 3rd Round | Stenhousemuir | 5-0 | Cove Rangers |
1st December 2009
| 3rd Round Replay | Peterhead | 1-4 | Raith Rovers |
28th November 2009
| 3rd Round | Albion Rovers | 1-0 | Elgin City |
| 3rd Round | Stirling Albion | 2-1 |
| 3rd Round | 1-0 | Arbroath |
| 3rd Round | Edinburgh City | 3-1 |
| 3rd Round | 4-4 | Brechin City |
| 3rd Round | Greenock Morton | 0-0 | Dumbarton |
| 3rd Round | Montrose | 2-1 | East Fife |
| 3rd Round | Raith Rovers | 0-0 | Peterhead |
| 3rd Round | 0-1 | Forfar Athletic |
| 3rd Round | Airdrie United | 4-0 | Queen of the South |
| 3rd Round | Ross County | 5-1 |
| 3rd Round | 1-2 |
| 3rd Round | 0-1 | Ayr United |
| 3rd Round | Cowdenbeath | 0-0 | Alloa Athletic |
31st October 2009
| 2nd Round Replay | 1-0 |
| 2nd Round Replay | 1-3 |
| 2nd Round Replay | 4-3 |
24th October 2009
| 2nd Round | Edinburgh City | 5-1 |
| 2nd Round | 0-2 | Albion Rovers |
| 2nd Round | 1-4 |
| 2nd Round | 0-3 |
| 2nd Round | Cove Rangers | 2-1 | Annan Athletic |
| 2nd Round | Forfar Athletic | 4-2 |
| 2nd Round | 1-3 |
| 2nd Round | 2-1 | Stranraer |
| 2nd Round | 1-1 |
| 2nd Round | 1-1 |
| 2nd Round | 1-4 |
| 2nd Round | 2-4 | Elgin City |
| 2nd Round | Queen's Park | 1-3 | Livingston |
| 2nd Round | 0-3 | Montrose |
| 2nd Round | 2-2 |
| 2nd Round | 1-2 |
3rd October 2009
| 1st Round Replay | 0-3 |
| 1st Round Replay | 2-1 |
| 1st Round Replay | 0-0 |
| 1st Round Replay | 1-2 |
26th September 2009
| 1st Round | 4-1 |
| 1st Round | 1-4 |
| 1st Round | 1-1 |
| 1st Round | 0-3 |
| 1st Round | 7-0 |
| 1st Round | 2-4 |
| 1st Round | 1-5 | Edinburgh City |
| 1st Round | 2-2 |
| 1st Round | 1-0 |
| 1st Round | 0-0 |
| 1st Round | 0-2 |
| 1st Round | 5-2 |
| 1st Round | 3-0 |
| 1st Round | 1-1 |
| 1st Round | 5-0 |
| 1st Round | 0-7 |
| 1st Round | 1-5 |