| Year | Winner | Runner-Up |
| 2023-24 | No season | No season |
| 2022-23 | No season | No season |
| 2021-22 | No season | No season |
| 2020-21 | No season | No season |
| 2019-20 | Season Void | Season Void |
| 2018-19 | No league | No league |
| 2017-18 | No league | No league |
| 2016-17 | No league | No league |
| 2015-16 | No league | No league |
| 2014-15 | No league | No league |
| 2013-14 | No league | No league |
| 2012-13 | No league | No league |
| 2011-12 | No league | No league |
| 2010-11 | No league | No league |
| 2009-10 | No league | No league |
| 2008-09 | No league | No league |
| 2007-08 | No league | No league |
| 2006-07 | No league | No league |
| 2005-06 | Rams Heid 1 | The Pageant |
| 2004-05 | No league | No league |
| 2003-04 | No league | No league |
| 2002-03 | Lordburn Bar 2 | Railway |
| 2001-02 | Station | Letham Hotel 2 |
| 2000-01 | Commercial (Letham) | Tutties 2 |
| 1999-00 | Corn Exchange | Breakers or Railway |
| 1998-99 | Ship Inn | West Port Bar |
| 1997-98 | Alma | Delaney's |
| 1996-97 | West Port Bar 2 | Stag 2 |
| 1995-96 | Railway | Foundry 1 |
| 1994-95 | Callaghans 2 | Foundry 2 |
| 1993-94 | Ship | Abbey 2 |
| 1992-93 | Abbey 3 | Imperial Hotel |
| 1991-92 | Crown Inn | Cliffburn Hotel |
| 1990-91 | Plough & Harrow | Delaney's 2 |
| 1989-90 | Delaney's | Sandy's 2 |
| 1988-89 | Newgate | A.S.C. Veterans |
| 1987-88 | Sandy's 3 | Malacca 2 |
| 1986-87 | Cliffburn 2 | Newgate 1 |
| 1985-86 | Portcullis 3 | Vics 3 |
| 1984-85 | A.S.C. 3 | Colliston |
| 1983-84 | Artisans | Alma 2 |
| 1982-83 | Imperial | Vics 2 |
| 1981-82 | Quaich | Newgate |
| 1980-81 | Fraser 4 | Viewfield 2 |
