| Year | Winner | Runner-Up |
| 2023-24 | Paddy Nicoll | Steve Hamilton |
| 2022-23 | Colin Brown | Ian Anderson |
| 2021-22 | Colin Brown | Greg Alexander |
| 2020-21 | No season | No season |
| 2019-20 | Season Void | Season Void |
| 2018-19 | Greg Alexander | Ryan Diplexcito |
| 2017-18 | David Jack | Christian Watt |
| 2016-17 | Greg Alexander | Michael Watt |
| 2015-16 | Steve Webster | Nick Denson |
| 2014-15 | David Jack | Greg Alexander |
| 2013-14 | Greg Alexander | Jonathan Cargill |
| 2012-13 | Gordon Dickson | Greg Alexander |
| 2011-12 | Steve Webster | Gary McLeish |
| 2010-11 | Gary McLeish | Steve Webster |
| 2009-10 | David Jack | Stuart Smith |
| 2008-09 | Scott Yeaman | Steve Hallam |
| 2007-08 | Dale Leith | Colin Brown |
| 2006-07 | Jonathan Cargill | Colin Brown |
| 2005-06 | Greg Alexander | David Williams |
| 2004-05 | Jonathan Cargill | Greg Alexander |
| 2003-04 | Greg Alexander | Charlie Cooper |
| 2002-03 | David Williams | David Jack |
| 2001-02 | George Fairweather | Paddy Nicoll |
| 2000-01 | Jonathan Cargill | Greg Alexander |
| 1999-00 | Steve Hallam | Gordon Smith |
| 1998-99 | Greg Alexander | Dave McPike |
| 1997-98 | George Fairweather | Colin Brown |
| 1996-97 | David Jack | Jonathan Cargill |
| 1995-96 | David Jack | Gordon Smith |
| 1994-95 | David McFarlane | George Fairweather |
| 1993-94 | Jonathan Cargill | Sandy McAllan |
| 1992-93 | John Hamilton | Dave McPike |
| 1991-92 | John Hamilton | Gordon Dickson |
| 1990-91 | John Hamilton | John Fotheringham |
| 1989-90 | John Hamilton | Steve Talbert |
| 1988-89 | Paul Bruce | John Fotheringham |
| 1987-88 | John Hamilton | Gordon Dickson |
| 1986-87 | George Fairweather | Rab Holden |
| 1985-86 | Rod Linton | Gordon Dickson |
| 1984-85 | George Fairweather | Gordon Dickson |
| 1983-84 | Derek Nicoll | Unknown |
| 1982-83 | Ronnie Edwards | Ian Spink |
| 1981-82 | John Laing | Graeme Ritchie |
