| 13/09/2008 14:00 | Albion Rovers | Dumbarton | (0-2) 1-3 | |
| 13/09/2008 14:00 | Cowdenbeath | Berwick | (2-0) 2-1 | |
| 13/09/2008 14:00 | East Stirling | Stenhousemuir | (0-1) 0-2 | |
| 13/09/2008 14:00 | Elgin | Annan Athletic | (0-1) 1-2 | |
| 13/09/2008 14:00 | Forfar | Montrose | (0-0) 0-1 | |
| 20/09/2008 14:00 | Annan Athletic | Forfar | (1-1) 1-3 | |
| 20/09/2008 14:00 | Dumbarton | Cowdenbeath | (1-0) 2-1 | |
| 20/09/2008 14:00 | Elgin | Albion Rovers | (0-2) 1-6 | |
| 20/09/2008 14:00 | Montrose | East Stirling | (1-0) 3-0 | |
| 20/09/2008 14:00 | Stenhousemuir | Berwick | (1-0) 2-0 | |
| 27/09/2008 14:00 | Albion Rovers | Stenhousemuir | (0-1) 1-2 | |
| 27/09/2008 14:00 | Berwick | Annan Athletic | (1-0) 3-0 | |
| 27/09/2008 14:00 | Cowdenbeath | Montrose | (1-1) 2-1 | |
| 27/09/2008 14:00 | East Stirling | Elgin | (3-1) 5-2 | |
| 27/09/2008 14:00 | Forfar | Dumbarton | (0-1) 2-2 |


