IFA Challenge Cup Winners
1999/00 Celtic
2000/01 Hibernian
2001/02 Queens Park Rangers
2002/03 Hibernian
2003/04 Ayr United
2004/05 Fulham
2005/06 Preston North End
2006/07 Hibernian
2007/08 Bury A
2008/09 Preston North End
2009/10 Preston North End
2010/11 Preston North End
2011/12 Kidderminster Harriers
2012/13 Preston North End
2013/14 Livingston GS
2014/15 West Bromwich Albion
2015/16 Rochdale
2016/17 Stirling Albion
2017/18 Livingston GS
2018/19 Troon
2019/20/21 Watford
2021/22 Motherwell
2022/23 Livingston GS
IFA Challenge Cup Runners-Up
1999/00
2000/01 Charlton Athletic
2001/02 Watford
2002/03 Kilmarnock
2003/04 Millwall
2004/05 Ayr United
2005/06 Nottingham Forest
2006/07 Bury
2007/08 Rochdale
2008/09 West Bromwich Albion
2009/10 West Bromwich Albion
2010/11 Kidderminster Harriers
2011/12 Ayr United
2012/13 Hearts
2013/14 Preston North End
2014/15 Runcorn Linnets
2015/16 Preston North End
2016/17 St Johnstone
2017/18 Rotherham United
2018/19 Rotherham United
2019/20/21 St Johnstone
2021/22 Preston North End
2022/23 Preston North End