Winners
1982/83 Loreburn Star
1983/84 Crown Athletic
1984/85 Nithside Colts
1985/86 Nithside Colts
1986/87 Cargenholm Rovers
1987/88 Kennedy Park Amateurs
1988/89 Kennedy Park Amateurs
1989/90 Kingholm Swan
1990/91 Stakeford
1991/92 Kennedy Park Amateurs
1992/93 Maxwelltown Eagles
1993/94 Maxwelltown Eagles
1994/95 Elopak
1995/96 Elopak
1996/97
1997/98 Blue Bell
1998/99
1999/00 Elopak
2000/01
2001/02 Castle Rovers
2002/03 Dynamo Star
2003/04 Waverly B
2004/05 Hole In The Wa
2005/06 Ruthwell Rovers
2006/07
2007/08 Balmoral
No 5-A-Sides have been played since 2007/08 season.