| 1975 | Kirkcaldy |
| 1976 | Stewart’s Melville FP |
| 1977 | Fauldhouse Victoria |
| 1978 | Cupar |
| 1979 | Holy Cross Academical |
| 1980 | Cupar |
| 1981 | Fauldhouse Victoria |
| 1982 | Leith Franklin |
| 1983 | Kirkcaldy |
| 1984 | Holy Cross Academical |
| 1985 | Cupar |
| 1986 | Grange |
| 1987 | Dunnikier |
| 1988 | Freuchie |
| 1989 | Stewart’s Melville FP |
| 1990 | Watsonian |
| 1991 | St Modan’s HSFP |
| 1992 | Corstorphine |
| 1993 | Cupar |
| 1994 | Falkland |
| 1995 | Stewart’s Melville FP |
| 1996 | Leith Franklin Academical |
| 1997 | Mitre |
| 1998 | Pakistan Association |
| 1999 | Dunnikier |
| 2000 | Holy Cross Academical |
| 2001 | Marchmont |
| 2002 | Fauldhouse Victoria |
| 2003 | Boroughmuir |
| 2004 | Holy Cross Academical |
| 2005 | Glenrothes |
| 2006 | Carlton Second XI |
| 2007 | Fauldhouse Victoria |
| 2008 | Largo |
| 2009 | Grange Second XI |
| 2010 | Marchmont |
| 2011 | Musselburgh |
| 2012 | St Boswells |
| 2013 | Gala |
| 2014 | Dunnikier |
| 2015 | Morton |
| 2016 | Edinburgh South |
| 2017 | Morton |
| 2018 | Edinburgh Second XI |
| 2019 | Drummond Trinity |
| 2020 | No competition |
| 2021 | Leith FAB |
| 2022 | Stewart’s Melville Second XI |
| 2023 | Clackmannan County |
Alan Veitch, Neil Leitch
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