30th May 2009
| Final | Rangers | 1-0 |
26th April 2009
| Semi Final | 2-0 |
25th April 2009
| Semi Final | Rangers | 3-0 | St. Mirren |
18th March 2009
| Quarter Final Replay | Aberdeen | 0-0 |
8th March 2009
| Quarter Final | Rangers | 5-1 |
7th March 2009
| Quarter Final | 0-1 |
| Quarter Final | 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 | 0-4 | Rangers |
17th February 2009
| 5th Round | 1-2 |
| 5th Round | Aberdeen | 5-0 |
7th February 2009
| 5th Round | Motherwell | 1-1 | St. Mirren |
| 5th Round | Celtic | 2-1 |
| 5th Round | 2-1 | Dundee United |
| 5th Round | 2-0 | Kilmarnock |
| 5th Round | Heart of Midlothian | 0-1 |
2nd February 2009
| 4th Round | 0-3 | Motherwell |
22nd January 2009
| 4th Round Replay | Kilmarnock | 3-1 |
20th January 2009
| 4th Round Replay | 1-0 |
13th January 2009
| 4th Round | 0-2 | Rangers |
| 4th Round | 1-3 | St. Mirren |
| 4th Round | 6-1 |
11th January 2009
| 4th Round | Hibernian | 0-2 | Heart of Midlothian |
| 4th Round | 0-4 | Dundee United |
10th January 2009
| 4th Round | 2-1 |
| 4th Round | Celtic | 2-1 |
| 4th Round | 3-0 |
| 4th Round | 4-2 |
| 4th Round | 0-1 |
| 4th Round | 2-0 |
| 4th Round | 2-2 | Kilmarnock |
| 4th Round | 2-2 |
| 4th Round | 0-1 |
| 4th Round | 1-2 | Aberdeen |
23rd December 2008
| 3rd Round Replay | 3-1 |
17th December 2008
| 3rd Round | 1-1 |
15th December 2008
| 3rd Round Replay | 2-4 |
| 3rd Round | 2-0 |
| 3rd Round Replay | 1-2 |
| 3rd Round | 1-2 |
13th December 2008
| 3rd Round | 4-0 |
9th December 2008
| 3rd Round Replay | 2-1 |
8th December 2008
| 3rd Round | 0-3 |
6th December 2008
| 3rd Round | 2-2 |
29th November 2008
| 3rd Round | 0-0 |
| 3rd Round | 2-0 |
| 3rd Round | 2-2 |
| 3rd Round | 2-1 |
| 3rd Round | 2-1 | Livingston |
| 3rd Round | 2-0 |
| 3rd Round | 2-3 |
| 3rd Round | 1-2 |
| 3rd Round | 0-5 |
| 3rd Round | 3-0 |
1st November 2008
| 2nd Round | 1-2 |
| 2nd Round Replay | 1-4 |
| 2nd Round Replay | 1-1 |
| 2nd Round | 0-1 |
26th October 2008
| 2nd Round | 4-2 |
25th October 2008
| 2nd Round | 0-1 |
| 2nd Round | 1-2 |
| 2nd Round | 1-3 |
| 2nd Round | 1-2 |
| 2nd Round | 3-0 |
| 2nd Round | 1-0 |
| 2nd Round | 2-0 |
| 2nd Round | 1-1 |
| 2nd Round | 6-0 |
| 2nd Round | 5-0 |
| 2nd Round | 1-0 |
| 2nd Round | 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 | 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 |