East Stirlingshire 2-3 Cowdenbeath *
| 16.05.2009 | Cowdenbeath | 1-1 | East Stirlingshire | |
| 13.05.2009 | East Stirlingshire | 1-2 | Cowdenbeath | |
Stenhousemuir FC 2-1 Queen's Park FC
| 17.05.2009 | Queen's Park FC | 0-0 | Stenhousemuir FC | |
| 14.05.2009 | Stenhousemuir FC | 2-1 | Queen's Park FC | |