15th March 2009
| Final | Rangers | 0-2 | Celtic |
28th January 2009
| Semi Final | Celtic | 0-0 | Dundee United |
27th January 2009
| Semi Final | Rangers | 3-0 |
29th October 2008
| Quarter Final | Kilmarnock | 1-3 | Celtic |
28th October 2008
| Quarter Final | Rangers | 2-0 |
| Quarter Final | 1-0 |
| Quarter Final | Dundee United | 1-0 |
24th September 2008
| 3rd Round | Kilmarnock | 4-2 | Aberdeen |
| 3rd Round | Motherwell | 1-2 |
| 3rd Round | 1-2 | Rangers |
23rd September 2008
| 3rd Round | Dundee United | 2-0 |
| 3rd Round | 2-0 | St. Mirren |
| 3rd Round | 2-1 |
| 3rd Round | Celtic | 4-0 | Livingston |
| 3rd Round | 1-2 |
27th August 2008
| 2nd Round | 0-2 | Kilmarnock |
| 2nd Round | Heart of Midlothian | 0-0 |
| 2nd Round | 0-1 | Aberdeen |
| 2nd Round | 2-2 |
26th August 2008
| 2nd Round | 1-0 |
| 2nd Round | Hibernian | 3-4 |
| 2nd Round | 1-3 |
| 2nd Round | 1-5 | Dundee United |
| 2nd Round | St. Mirren | 7-0 |
| 2nd Round | 1-2 |
| 2nd Round | Livingston | 2-1 |
| 2nd Round | 3-1 |
6th August 2008
| 1st Round | 2-1 |
| 1st Round | 0-3 |
| 1st Round | 1-2 | Livingston |
| 1st Round | 3-2 |
5th August 2008
| 1st Round | 2-3 |
| 1st Round | 2-0 |
| 1st Round | 4-3 |
| 1st Round | 0-2 |
| 1st Round | 3-6 |
| 1st Round | 0-2 |
| 1st Round | 4-1 |
| 1st Round | 0-0 |
| 1st Round | 1-5 |
| 1st Round | 1-1 |