Mark Warburton and Jim McInally are hoping to lead their teams to Petrofac Training Cup success when Rangers play Peterhead on Sunday.
We continue our countdown to the big game by looking at the previous winning bosses.
Terry Christie is the only manager to have achieved the feat twice, with Stenhousemuir in 1995/96 and Alloa four years later.
List of winning managers
1990/91 Gordon Wallace (Dundee)
1991/92 Billy McLaren (Hamilton Accies)
1992/93 Iain Munro (Hamilton Accies)
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)
2000/01 Steve Archibald (Airdrie)
2001/02 Ian McCall (Airdrie)
2002/03 John Connolly (Queen of the South)
2003/04 John Robertson (Inverness Caley 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)
