| 06/12/2008 | Ross County | Dunfermline | Post | |
| 06/12/2008 15:00 | Saint Johnstone | Queen of the South | (0-0) 0-0 | |
| 10/12/2008 | Livingston | Dundee | Post | |
| 13/12/2008 15:00 | Clyde | Dundee | (0-0) 1-0 | |
| 13/12/2008 15:00 | Partick Thistle | Airdrie United | (1-1) 2-1 | |
| 13/12/2008 15:00 | Queen of the South | Dunfermline | (1-1) 1-2 | |
| 13/12/2008 15:00 | Ross County | Livingston | (1-1) 1-4 | |
| 13/12/2008 15:00 | Saint Johnstone | Morton | (0-0) 1-0 | |
| 16/12/2008 19:45 | Clyde | Airdrie United | (0-0) 1-0 | |
| 20/12/2008 15:00 | Airdrie United | Saint Johnstone | (0-0) 1-1 | |
| 20/12/2008 15:00 | Dundee | Partick Thistle | (0-0) 0-0 | |
| 20/12/2008 15:00 | Dunfermline | Clyde | (1-1) 4-4 | |
| 20/12/2008 15:00 | Livingston | Queen of the South | (0-0) 2-0 | |
| 20/12/2008 15:00 | Morton | Ross County | (1-1) 2-1 | |
| 27/12/2008 15:00 | Airdrie United | Morton | (1-0) 1-0 | |
| 27/12/2008 15:00 | Partick Thistle | Ross County | (0-1) 0-2 | |
| 27/12/2008 15:00 | Queen of the South | Dundee | (0-1) 0-1 | |
| 27/12/2008 15:00 | Saint Johnstone | Clyde | (1-0) 1-0 | |
| 30/12/2008 19:30 | Morton | Partick Thistle | (1-0) 2-0 | |
| 30/12/2008 19:45 | Dunfermline | Livingston | (0-0) 1-0 |


