| Year | Winner | Runner-Up |
| 2023-24 | Letham | Ram's Heid |
| 2022-23 | The Fab Bar | Letham |
| 2021-22 | Legion 2 | Shotz 2 |
| 2020-21 | No season | No season |
| 2019-20 | Season Void | Season Void |
| 2018-19 | West Port Bar | St Tams |
| 2017-18 | Ram's Heid 2 | Buicks Bar |
| 2016-17 | Ram's Heid 1 | Legion 1 |
| 2015-16 | Ram's Heid 2 | Portcullis 3 |
| 2014-15 | Shotz 3 | West Port Bar 1 |
| 2013-14 | Burns Bar | Railway 2 |
| 2012-13 | Bowlers | Legion 3 |
| 2011-12 | Stag | Station |
| 2010-11 | Legion 1 | Portcullis 3 |
| 2009-10 | Stag | Fishermans ^ |
| 2008-09 | Legion 1 | Newgate |
| 2007-08 | Letham Hotel | Stag |
| 2006-07 | Railway Inn | Crown 2 * |
| 2005-06 | Station ^ | Burns Bar 2 |
| 2004-05 | Letham Hotel | Portcullis 2 |
| 2003-04 | Stag | Newgate |
| 2002-03 | Station | Plough |
| 2001-02 | Commericial (Letham) | Abbey 2 |
| 2000-01 | Newgate | Lordburn Bar 2 |
| 1999-00 | West Port Bar | Fishermans |
| 1998-99 | Plough & Harrow | Liberty's |
| 1997-98 | St Tam's Bar | Stag |
| 1996-97 | Crown | Viewfield 2 |
| 1995-96 | Abbey 2 | Tutties 1 |
| 1994-95 | Ship 2 | Portcullis 3 |
| 1993-94 | Ram's Heid | A.S.C. Veterans |
| 1992-93 | A.S.C. 3 | Portcullis 2 |
| 1991-92 | Plough & Harrow | Ram's Heid 2 |
| 1990-91 | Delaney's 1 | A.S.C. 3 |
| 1989-90 | Portcullis 1 | A.S.C. 1 |
| 1988-89 | Sandy's | Malacca 1 |
| 1987-88 | Newgate | Crown 1 |
| 1986-87 | Portcullis 3 | Vics |
| 1985-86 | A.S.C. 3 | Scotia |
| 1984-85 | Viewfield 2 | A.S.C. 1 |
| 1983-84 | Malacca | Vics 2 |
| 1982-83 | Fraser's 2 | Ram's Heid 3 |
| 1981-82 | Viewfield | Dunnichen |
| 1980-81 | Ram's Heid 4 | Angus Bar |
| 1979-80 | Fraser's 3 | Auchmithie |
| * After play-off with Letham Hotel 1 | ||
| ^ After play-off with Burns Bar 2 | ||
