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2000/2001
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Archive
Season
Winner
Challenge Cup 2025/2026
Challenge Cup 2024/2025
Livingston
Challenge Cup 2023/2024
Airdrieonians
Challenge Cup 2022/2023
Hamilton
Challenge Cup 2021/2022
Raith
Challenge Cup 2019/2020
Raith
Inverness
Challenge Cup 2018/2019
Ross County
Challenge Cup 2017/2018
Inverness
Challenge Cup 2016/2017
Dundee Utd
Challenge Cup 2015/2016
Rangers
Challenge Cup 2014/2015
Livingston
Challenge Cup 2013/2014
Raith
Challenge Cup 2012/2013
Queen of South
Challenge Cup 2011/2012
Falkirk
Challenge Cup 2010/2011
Ross County
Challenge Cup 2009/2010
Dundee FC
Challenge Cup 2008/2009
Airdrieonians
Challenge Cup 2007/2008
St Johnstone
Challenge Cup 2006/2007
Ross County
Challenge Cup 2005/2006
St. Mirren
Challenge Cup 2004/2005
Falkirk
Challenge Cup 2003/2004
Inverness
Challenge Cup 2002/2003
Queen of South
Challenge Cup 2001/2002
Airdrieonians
Challenge Cup 2000/2001
Airdrieonians
Challenge Cup 1999/2000
Alloa
