This season's final is between Connah's Quay Nomads, managed by Andy Morrison, and Ross County, who have co-managers in Steven Ferguson and Stuart Kettlewell.
Winning managers
1990/91: Gordon Wallace (Dundee)
1991/92: Billy McLaren (Hamilton Academical)
1992/93: Iain Munro (Hamilton Academical)
1993/94: Jim Jefferies (Falkirk)
1994/95: Alex MacDonald (Airdrie)
1995/96: Terry Christie (Stenhousemuir)
1996/97: Campbell Money (Stranraer)
1997/98: Alex Totten (Falkirk)
1998/99: Competition not held
1999/00: Terry Christie (Alloa Athletic)
2000/01: Steve Archibald (Airdrie)
2001/02: Ian McCall (Airdrie)
2002/03: John Connolly (Queen of the South)
2003/04: John Robertson (Inverness Caledonian Thistle)
2004/05: John Hughes (Falkirk)
2005/06: Gus MacPherson (St Mirren)
2006/07: Scott Leitch (Ross County)
2007/08: Sandy Stewart (St Johnstone)
2008/09: Kenny Black (Airdrie)
2009/10: Jocky Scott (Dundee)
2010/11: Jimmy Calderwood (Ross County)
2011/12: Steven Pressley (Falkirk)
2012/13: Allan Johnston (Queen of the South)
2013/14: Grant Murray (Raith Rovers)
2014/15: Mark Burchill (Livingston)
2015/16: Mark Warburton (Rangers)
2016/17: Ray McKinnon (Dundee United)
2017/18: John Robertson (Inverness Caledonian Thistle)
