23rd May 2009
| Final 2nd Leg | Stenhousemuir | 0-0 | Cowdenbeath |
20th May 2009
| Final 1st Leg | Cowdenbeath | 0-0 | Stenhousemuir |
17th May 2009
| Semi Final 2nd Leg | Queen's Park | 0-0 | Stenhousemuir |
16th May 2009
| Semi Final 2nd Leg | Cowdenbeath | 1-1 |
14th May 2009
| Semi Final 1st Leg | Stenhousemuir | 2-1 | Queen's Park |
13th May 2009
| Semi Final 1st Leg | 1-2 | Cowdenbeath |