2018/2019
Alloa Athletic
Challenge Cup
2018/2019
Alloa Athletic
League Cup
2017/2018
Albion Rovers
League Cup
2017/2018
Albion Rovers
Challenge Cup
2016/2017
Brechin City
League Cup
2015/2016
Ayr United
League Cup
2015/2016
Ayr United
Challenge Cup
2014/2015
Brechin City
League Cup
2014/2015
Brechin City
Challenge Cup
2013/2014
Brechin City
League Cup
2013/2014
Brechin City
Challenge Cup
2011/2012
Ayr United
League Cup
2011/2012
Ayr United
Challenge Cup
2010/2011
Ayr United
League Cup
2010/2011
Ayr United
Challenge Cup
2009/2010
Airdrieonians
League Cup
2009/2010
Airdrieonians
Challenge Cup
2008/2009
Clyde
Challenge Cup
01.07.18
Albion
Alloa Athletic
Free
01.07.17
Brechin
Albion
Free
01.07.16
Ayr Utd
Brechin
Free
01.07.15
Brechin
Ayr Utd
N/A
28.07.12
Ayr Utd
Brechin
N/A