24th May 2009
| Final 2nd Leg | Airdrie United | 0-1 | Ayr United |
20th May 2009
| Final 1st Leg | Ayr United | 2-2 | Airdrie United |
17th May 2009
| Semi Final 2nd Leg | Airdrie United | 2-1 | Peterhead |
16th May 2009
| Semi Final 2nd Leg | Ayr United | 3-2 | Brechin City |
14th May 2009
| Semi Final 1st Leg | Peterhead | 0-2 | Airdrie United |
13th May 2009
| Semi Final 1st Leg | Brechin City | 0-2 | Ayr United |