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