| 01/11/2008 15:00 | Albion Rovers | Cowdenbeath | (1-0) 3-1 | |
| 01/11/2008 15:00 | Dumbarton | Berwick | (3-1) 5-2 | |
| 01/11/2008 15:00 | Elgin | Forfar | (0-1) 0-1 | |
| 01/11/2008 15:00 | Montrose | Stenhousemuir | (0-2) 0-3 | |
| 08/11/2008 15:00 | Annan Athletic | Montrose | (1-1) 1-2 | |
| 08/11/2008 15:00 | Berwick | Albion Rovers | (0-1) 0-3 | |
| 08/11/2008 15:00 | Cowdenbeath | Elgin | (3-1) 4-1 | |
| 08/11/2008 15:00 | Forfar | East Stirling | (2-2) 2-3 | |
| 08/11/2008 15:00 | Stenhousemuir | Dumbarton | (0-0) 1-1 | |
| 12/11/2008 19:30 | East Stirling | Annan Athletic | (0-1) 2-1 | |
| 15/11/2008 15:00 | Albion Rovers | Annan Athletic | (0-1) 0-1 | |
| 15/11/2008 15:00 | Cowdenbeath | Stenhousemuir | (0-2) 1-2 | |
| 15/11/2008 15:00 | East Stirling | Dumbarton | (2-0) 5-2 | |
| 15/11/2008 15:00 | Elgin | Montrose | (0-0) 1-2 | |
| 15/11/2008 15:00 | Forfar | Berwick | (1-1) 2-1 | |
| 22/11/2008 15:00 | Annan Athletic | Elgin | (1-0) 5-0 | |
| 22/11/2008 15:00 | Berwick | Cowdenbeath | (1-1) 2-3 | |
| 22/11/2008 15:00 | Dumbarton | Albion Rovers | (1-1) 1-1 | |
| 22/11/2008 15:00 | Montrose | Forfar | (1-0) 1-0 | |
| 22/11/2008 15:00 | Stenhousemuir | East Stirling | (0-1) 1-1 |


