30th May 2009
| Final | Rangers | 1-0 | Falkirk |
26th April 2009
| Semi Final | Falkirk | 2-0 | Dunfermline Athletic |
25th April 2009
| Semi Final | Rangers | 3-0 | St. Mirren |
18th March 2009
| Quarter Final Replay | Aberdeen | 0-0 | Dunfermline Athletic |
8th March 2009
| Quarter Final | Rangers | 5-1 |
7th March 2009
| Quarter Final | Inverness Caledonian Thistle | 0-1 | Falkirk |
| Quarter Final | Dunfermline Athletic | 1-1 | Aberdeen |
| Quarter Final | St. Mirren | 1-0 | Celtic |
19th February 2009
| 5th Round Replay | St. Mirren | 1-0 | Motherwell |
18th February 2009
| 5th Round | Forfar Athletic | 0-4 | Rangers |
17th February 2009
| 5th Round | Airdrie United | 1-2 | Dunfermline Athletic |
| 5th Round | Aberdeen | 5-0 | East Fife |
7th February 2009
| 5th Round | Motherwell | 1-1 | St. Mirren |
| 5th Round | Celtic | 2-1 | Queen's Park |
| 5th Round | 2-1 | Dundee United |
| 5th Round | Inverness Caledonian Thistle | 2-0 | Kilmarnock |
| 5th Round | Heart of Midlothian | 0-1 | Falkirk |
2nd February 2009
| 4th Round | 0-3 | Motherwell |
22nd January 2009
| 4th Round Replay | Kilmarnock | 3-1 | Ayr United |
20th January 2009
| 4th Round Replay | Queen's Park | 1-0 | Peterhead |
13th January 2009
| 4th Round | St. Johnstone | 0-2 | Rangers |
| 4th Round | Brechin City | 1-3 | St. Mirren |
| 4th Round | Forfar Athletic | 6-1 |
11th January 2009
| 4th Round | Hibernian | 0-2 | Heart of Midlothian |
| 4th Round | 0-4 | Dundee United |
10th January 2009
| 4th Round | Airdrie United | 2-1 |
| 4th Round | Celtic | 2-1 | Dundee |
| 4th Round | Inverness Caledonian Thistle | 3-0 | Partick Thistle |
| 4th Round | Falkirk | 4-2 | Queen of the South |
| 4th Round | Ross County | 0-1 |
| 4th Round | Dunfermline Athletic | 2-0 | Clyde |
| 4th Round | Ayr United | 2-2 | Kilmarnock |
| 4th Round | Peterhead | 2-2 | Queen's Park |
| 4th Round | Stenhousemuir | 0-1 | East Fife |
| 4th Round | Alloa Athletic | 1-2 | Aberdeen |
23rd December 2008
| 3rd Round Replay | Ayr United | 3-1 |
17th December 2008
| 3rd Round | 1-1 | Ayr United |
15th December 2008
| 3rd Round Replay | 2-4 |
| 3rd Round | Forfar Athletic | 2-0 | Stranraer |
| 3rd Round Replay | Dumbarton | 1-2 | Ross County |
| 3rd Round | Elgin City | 1-2 |
13th December 2008
| 3rd Round | 4-0 |
9th December 2008
| 3rd Round Replay | Alloa Athletic | 2-1 | Raith Rovers |
8th December 2008
| 3rd Round | Edinburgh City | 0-3 | Brechin City |
6th December 2008
| 3rd Round | 2-2 |
29th November 2008
| 3rd Round | Raith Rovers | 0-0 | Alloa Athletic |
| 3rd Round | East Fife | 2-0 | Arbroath |
| 3rd Round | Ross County | 2-2 | Dumbarton |
| 3rd Round | Peterhead | 2-1 | Greenock Morton |
| 3rd Round | 2-1 |
| 3rd Round | Clyde | 2-0 | Montrose |
| 3rd Round | Stirling Albion | 2-3 | Partick Thistle |
| 3rd Round | Albion Rovers | 1-2 | Queen's Park |
| 3rd Round | 0-5 | Stenhousemuir |
| 3rd Round | Airdrie United | 3-0 | Cove Rangers |
1st November 2008
| 2nd Round | Annan Athletic | 1-2 |
| 2nd Round Replay | 1-4 | Edinburgh City |
| 2nd Round Replay | 1-1 |
| 2nd Round | 0-1 |
26th October 2008
| 2nd Round | 4-2 |
25th October 2008
| 2nd Round | 0-1 | Dumbarton |
| 2nd Round | Cowdenbeath | 1-2 | Elgin City |
| 2nd Round | 1-3 | Forfar Athletic |
| 2nd Round | 1-2 | Albion Rovers |
| 2nd Round | 3-0 |
| 2nd Round | Cove Rangers | 1-0 |
| 2nd Round | Montrose | 2-0 |
| 2nd Round | 1-1 |
| 2nd Round | 6-0 |
| 2nd Round | Stenhousemuir | 5-0 |
| 2nd Round | 1-0 |
| 2nd Round | Edinburgh City | 0-0 |
| 2nd Round | 5-1 |
4th October 2008
| 1st Round Replay | 2-2 |
| 1st Round Replay | 2-1 |
| 1st Round Replay | 1-0 |
| 1st Round Replay | 2-0 |
27th September 2008
| 1st Round | 6-3 |
| 1st Round | 1-1 |
| 1st Round | 2-2 |
| 1st Round | 5-2 |
| 1st Round | 1-1 |
| 1st Round | 0-3 |
| 1st Round | 5-1 |
| 1st Round | 1-2 |
| 1st Round | 1-3 |
| 1st Round | Edinburgh City | 2-0 |
| 1st Round | 0-3 |
| 1st Round | 10-0 |
| 1st Round | 4-0 |
| 1st Round | 1-0 |
| 1st Round | 3-1 |
| 1st Round | 3-1 |
| 1st Round | 1-1 |
| 1st Round | 1-0 |