League Winners
| 1991-92 | GOLF | ||
| 1990-91 | GOLF 2 | ||
| 1989-90 | GOLF 2 | ||
| 1988-89 | WHITE HOOSE 2 | ||
| 1987-88 | GOLF 1 | ||
| 1986-87 | FIFE ARMS | ||
| 1985-86 | KENNOWAY LEGION | ||
| 1984-85 | BALGONIE B.C. 2 | ||
| 1983-84 | GOLF 2 | ||
| 2009-10 | 1982-83 | GOLF 2 | |
| 2008-09 | BRIG | 1981-82 | RAILWAY 1 |
| 2007-08 | SUNBEAM | 1980-81 | GOLF 2 |
| 2006-07 | AULD HOOSE BUCKHAVEN | 1979-80 | GOLF 2 |
| 2005-06 | RAILWAY | 1978-79 | KENNOWAY B.C. 1 |
| 2004-05 | AULD HOOSE BUCKHAVEN AULD HOOSE BUCKHAVEN | 1977-78 | GOLF 2 |
| 2003-04 | RAILWAY | 1976-77 | WINDYGATES HOTEL |
| 2002-03 | RAILWAY | 1975-76 | AULD HOOSE WINDYGATES |
| 2001-02 | RAILWAY 1 | 1974-75 | METHILHILL EX-SERVICES |
| 2000-01 | RAILWAY | 1973-74 | METHILHILL EX-SERVICES |
| 1999-00 | RAILWAY | 1972-73 | AULD HOOSE WINDYGATES |
| 1998-99 | RAILWAY | 1971-72 | |
| 1997-98 | RAILWAY | 1970-71 | KENNOWAY LEGION |
| 1996-97 | DOUGLAS ARMS B | 1969-70 | KENNOWAY LEGION |
| 1995-96 | GOLF | 1968-69 | GOLF 1 |
| 1994-95 | GOLF | 1967-68 | GOLF 1 |
| 1993-94 | GOLF | 1966-67 | GOLF 1 |
| 1992-93 | GOLF | 1965-66 | GOLF 1 |
