SIXES WINNERS
| 1999-00 | RAILWAY | ||
| 1998-99 | FIFE ARMS | ||
| 1997-98 | RAILWAY | ||
| 1996-97 | DOUGLAS ARMS B | ||
| 1995-96 | GOLF | ||
| 1994-95 | GOLF | ||
| 2009-10 | 1993-94 | GOLF | |
| 2008-09 | SUNBEAM | 1992-93 | GOLF |
| 2007-08 | SUNBEAM | 1991-92 | GOLF |
| 2006-07 | RAILWAY | 1990-91 | FIFE ARMS |
| 2005-06 | AULD HOOSE BUCKHAVEN | 1989-90 | GOLF 2 |
| 2004-05 | McPHAILS | 1988-89 | GOLF 2 |
| 2003-04 | AULD HOOSE BUCKHAVEN | 1987-88 | FIFE ARMS |
| 2002-03 | RAILWAY | 1986-87 | KENNOWAY LEGION 1 |
| 2001-02 | RAILWAY 1 | 1985-86 | KENNOWAY COMMUNITY 1 |
| 2000-01 | RAILWAY | 1984-85 | KENNOWAY LEGION 1 |
