Daryl:
5
1996-97
2000-01
2011-12
2018-19
2023-24
Steve:
5
1999-00
2003-04
2007-08
2013-14
2020-21
Cobman:
5
2001-02
2002-03
2012-13
2014-15
2017-18
Dave:
4
2004-05
2008-09
2009-10
2010-11
Matt:
3
2021-22
2022-23
2024-25
Stuart:
3
1995-96
2005-06
2015-16
Ewen:
2
2016-17
2019-20
Unknown :
2
1997-98
1998-99
Sean:
1
1994-95
Rich:
1
2006-07
| KSSL | Year | Winner |
| XXXI | 2024-25 | Matt |
| XXX | 2023-24 | Daryl |
| XXIX | 2022-23 | Matt |
| XXVIII | 2021-22 | Matt |
| XXVII | 2020-21 | Steve |
| XXVI | 2019-20 | Ewen |
| XXV | 2018-19 | Daryl |
| XXIV | 2017-18 | Cobman |
| XXIII | 2016-17 | Ewen |
| XXII | 2015-16 | Stuart |
| XXI | 2014-15 | Cobman |
| XX | 2013-14 | Steve |
| XIX | 2012-13 | Cobman |
| XVIII | 2011-12 | Daryl |
| XVII | 2010-11 | Dave |
| XVI | 2009-10 | Dave |
| XV | 2008-09 | Dave |
| XIV | 2007-08 | Steve |
| XIII | 2006-07 | Rich |
| XII | 2005-06 | Stuart |
| XI | 2004-05 | Dave |
| X | 2003-04 | Steve |
| IX | 2002-03 | Cobman |
| VIII | 2001-02 | Cobman |
| VII | 2000-01 | Daryl |
| VI | 1999-00 | Steve |
| V | 1998-99 | Unknown |
| IV | 1997-98 | Unknown |
| III | 1996-97 | Daryl |
| II | 1995-96 | Stuart |
| I | 1994-95 | Sean |