Main Mens
| Year | Mens A |
| 2023 | Nick Mulvey |
| 2022 | Rui Soares |
| 2021 | No Competition |
| 2020 | No Competition |
| 2019 | Adrian Waller |
| 2018 | Adrian Waller |
| 2017 | Nick Mulvey |
| 2016 | Angus Gillams |
| 2015 | Adrian Waller |
| 2014 | Adrian Waller |
| 2013 | Angus Gillams |
| 2011/12 | Keith Timms |
| 2010/11 | Adrian Waller |
| 2009/10 | Chris Ryder |
| 2008/09 | Marc Woolhead |
| 2007/08 | Adrian Waller |
| 2006 | Adrian Waller |
| 2005 | Marc Woolhead |
| 2004 | Jason Foster |
| 2003 | Keith Timms |
| 2002 | Jason Foster |
| 2001 | Chris Ryder |
| 2000 | Chris Ryder |
| 1999 | Galen Le Chaminant |
| 1998 | Paul Carter |
| 1997 | Paul Carter |
| 1996 | Paul Carter |
| 1995 | Paul Carter |
| 1994 | Paul Carter |
| 1993 | Paul Carter |
| 1992 | Paul Carter |
| 1992 | Paul Carter |
| 1991 | J Davis |
| 1990 | Simon Krystman |
| 1989 | Gehan Fernando |
| 1988 | Paul Carter |
| 1987 | Simon Krystman |
| 1986 | Paul Carter |
| 1985 | Paul Carter |
| 1984 | Paul Carter |
| 1983 | Dave Sanders |
| 1982 | Hugh Colburn |
| 1981 | Hugh Colburn |
| 1980 | Derek Thorpe |
| 1979 | Dave Sanders |
| 1978 | Hugh Colburn |
| 1977 | Hugh Colburn |
| 1976 | Chris H Stahl |
| 1975 | Hugh Colburn |
| 1974 | Hugh Colburn |
| 1973 | C H Stahl |
| 1972 | Stuart H Courtney |
| 1971 | Stuart H Courtney |
| 1970 | C H Stahl |
| 1969 | C H Stahl |
| 1968 | J E A Mocatta |
| 1967 | R M H Boddington |
| 1966 | R M H Boddington |
| 1965 | R M H Boddington |
| 1964 | R M H Boddington |
| 1963 | R N Harrison |
| 1962 | M Macbean |
| 1961 | M E Kingston |
| 1960 | R M H Boddington |
| 1959 | R M H Boddington |
| 1958 | M E Kingston |
| 1957 | R A H Fletcher |
| 1956 | R M H Boddington |
| 1955 | W H Mallett |
| 1954 | W H Mallett |
| 1953 | W H Mallett |
| 1952 | W T Atkins |
| 1951 | W T Atkins |
| 1950 | J R C Yglesias |
| 1949 | J R C Yglesias |
| 1948 | J R C Yglesias |
| 1939 | P G W S Fuljamee |
| 1938 | GG Lawrence |
| 1937 | GG Lawrence |
Main Ladies
| Year | Ladies |
| 2023 | Mhairi Gritz |
| 2022 | Grace Gear |
| 2021 | No Competition |
| 2020 | No Competition |
| 2019 | Nyah Williams |
| 2018 | Grace Gear |
| 2017 | Grace Gear |
| 2016 | Cathy Abernethy |
| 2015 | Cathy Abernethy |
| 2014 | Ali Hemingway |
| 2013 | Brogan Lane |
| 2011/12 | Maureen Morrison |
| 2010/11 | Brogan Lane |
| 2009/10 | Brogan Lane |
| 2008/09 | Brogan Lane |
| 2007 | Isobel Smith |
| 2006 | Isobel Smith |
| 2005 | Maureen Morrison |
| 2004 | Zoe Durbach |
| 2003 | Zoe Smith |
| 2002 | Isobel Smith |
| 2001 | Zoe Smith |
| 2000 | Isobel Smith |
| 1999 | Sue Littler |
| 1998 | Sue Littler |
| 1997 | Sue Littler |
| 1996 | Sue Littler |
| 1995 | Sue Littler |
| 1994 | Sally Ann Riley |
| 1993 | Sue Littler |
| 1992 | Sue Littler |
Mens B Competition
| Year | Mens B |
| 2023 | Mark Godfrey-Evans |
| 2022 | Bilal Ahmed |
| 2021 | No Competition |
| 2020 | No Competition |
| 2019 | Vig Gunasegaran |
| 2018 | Paul Cousins |
| 2017 | Alex O’Sullivan |
| 2016 | Paul Cousins |
| 2015 | Dan Ludlam |
| 2014 | Dan Ludlam |
| 2013 | James Clyne |
| 2011/12 | Jack Fowler |
| 2010/11 | Jack Fowler |
| 2009/10 | Peter Newman |
| 2008/9 | James Clyne |
| 2007/8 | Nathan Derrick |
| 2006/7 | Aron Toms |
| 2005 | Gavin Noffki |
| 2004 | |
| 2003 | |
| 2002 | Tony Stewart |
| 2001 | Mike Philp |
| 2000 | Tony Stewart |
| 1999 | Keith Timms |
| 1998 | Jonathan Quail |
| 1997 | Tony Stewart |
| 1996 | Pat Offei |
Mens C Competition
| Year | Mens C |
| 2023 | Nick Cooper |
| 2022 | Nick Cooper |
| 2021 | No Competition |
| 2020 | No Competition |
| 2019 | Nick Cooper |
| 2018 | Zan Farooqi |
| 2017 | Dave Mcmahon |
| 2016 | Tom Elliott |
| 2015 | Thomas Horton |
| 2014 | Owen Ledger |
| 2013 | Tom Lo |
| 2011/12 | Pat Offei |
| 2010/11 | Bradley Whitbread |
| 2009/10 | Ian Gould |
| 2008/9 | Martin Nash |
| 2007/8 | Ian Blower |
| 2006/7 | Ian Blower |
| 2005 | James Clyne |
Mens O35
| Year | Mens O’35 |
| 2023 | Vig Gunasegaran |
| 2022 | Paul Cousins |
| 2021 | No Competition |
| 2020 | No Competition |
| 2019 | Ali Coker |
| 2018 | Keith Timms |
| 2017 | Keith Timms |
| 2016 | Ali Coker |
| 2015 | Ali Coker |
| 2014 | No Competition |
| 2013 | Mark Woolhead |
| 2011/12 | Nick Lavery |
| 2010/11 | Ali Coker |
| 2009/10 | Scott Rickard |
| 2008/09 | Nick Lavery |
| 2007/08 | John Mcfarlane |
| 2006 | John Mcfarlane |
| 2005 | John Mcfarlane |
| 2004 | Jason Foster |
| 2003 | Martin Geear |
| 2002 | Martin Geear |
| 2001 | Martin Geear |
| 2000 | Paul Ryan |
| 1999 | Marvin Rust |
| 1998 | Dave Sanders |
| 1997 | Dave Sanders |
| 1996 | Steve Morris |
| 1995 | Dave Sanders |
| 1994 | Derek Thorpe |
| 1993 | No Competition |
| 1992 | Derek Thorpe |
Mens O45
| Year | O’45/Vets |
| 2023 | Ryan Fitzsimon |
| 2022 | Andy Duckworth |
| 2021 | No Competition |
| 2020 | No Competition |
| 2019 | Eamonn Price |
| 2018 | Steve Lloyd |
| 2017 | Eamonn Price |
| 2016 | Peter Newman |
| 2015 | Tony Stewart |
| 2014 | Peter Newman |
| 2013 | Marvin Rust |
| 2011/12 | Marvin Rust |
| 2010/11 | Eamonn Price |
| 2009/10 | Eamonn Price |
| 2008/09 | Eamonn Price |
| 2007/08 | Gary Spindler |
| 2006 | Gary Spindler |
| 2005 | Paul Ryan |
| 2004 | Peter Leary |
| 2003 | Peter Leary |
| 2002 | Derek Thorpe |
| 2001 | Peter Leary |
| 2000 | Peter Leary |
| 1999 | Peter Leary |
| 1998 | Derek Thorpe |
| 1997 | Derek Thorpe |
| 1996 | Dave Cooper |
| 1995 | Alan Gammage |
| 1994 | Tony Clifford |
| 1993 | |
| 1992 | Dave Cording |
Womens O40
| Year | Ladies O40 |
| 2023 | Jillian Lilico |
| 2022 | Libby Montgomery |
| 2021 | No Competition |
| 2020 | No Competition |
| 2019 | Isobel Smith |
| 2018 | Sheila Blake |
| 2017 | Sheila Blake |
| 2016 | Libby Montgomery |
| 2015 | Maureen Morrison |
| 2014 | Isobel Smith |
| 2013 | |
| 2011/12 | |
| 2010/11 | |
| 2009/10 | |
| 2008/09 | |
| 2007 | Elke Rubasm |
| 2006 | Elke Rubasm |
| 2005 | Elke Rubsam |
| 2004 | Maureen Winter |
| 2003 | Lesley Garner |
| 2002 | Lesley Garner |
| 2001 | Lesley Garner |
| 2000 | Sue Littler |
| 1999 | Sue Littler |
| 1998 | Sue Littler |
| 1997 | Sue Littler |
| 1996 | Sue Littler |
| 1995 | Elke Rubsam |
| 1994 | Betty Longhurst |
| 1993 | |
| 1992 | June Peterson |
Mens O55
| Year | O’55 |
| 2023 | Teejay Sogunro |
| 2022 | Teejay Sogunro |
| 2021 | No Competition |
| 2020 | No Competition |
| 2019 | Eamonn Price |
| 2018 | Teejay Sogunro |
| 2017 | Julian Craxton |
| 2016 | Julian Craxton |
| 2015 | Gary Spindler |
| 2014 | David Wells |
| 2013 | David Wells |
| 2011/12 | Peter Farr |
| 2010/11 | Peter Leary |
| 2009/10 | Phil Collins btKeith Wragg |
| 2008/09 | Dave Cooper |
| 2007/08 | Bill Nissell |
| 2006 | Dave Cooper |
| 2005 | Dave Cooper |
| 2004 | |
| 2003 | |
| 2002 | |
| 2001 | |
| 2000 | |
| 1999 | |
| 1998 | |
| 1997 | |
| 1996 | |
| 1995 | Graham Littler |
Mens O65
| Year | O’65 Vint |
| 2023 | Julian Craxton |
| 2022 | Julian Craxton |
| 2021 | No Competition |
| 2020 | No Competition |
| 2019 | Peter Quarman |
| 2018 | No Competition |
| 2017 | John Lewis |
| 2016 | No Competition |
| 2015 | No Competition |
| 2014 | No Competition |
| 2013 | |
| 2011/12 | Tony Clifford |
| 2010/11 | Tony Clifford |
| 2009/10 | Tony Clifford |
| 2008/09 | Tony Clifford btLen Froggitt |
| 2007/08 | Len Froggitt (RR) |
| 2006 | Len Froggitt (RR) |
| 2005 | John Preston |
| 2004 | M J Newton |
| 2003 | G Ball |
| 2002 | G Ball |
| 2001 | Tony Clifford |
| 2000 | Tony Clifford |
| 1999 | Tony Clifford |
| 1998 | Tony Clifford |
| 1997 | Len Froggitt |
| 1996 | Len Froggitt |
| 1995 | Graham Littler |
| 1994 | Alf Linskey |
| 1993 | Graham Littler |
| 1992 | Graham Littler |
Racketball
| 2023 | Adam Grilli |
| 2022 | Adam Grilli |
| 2021 | No Competition |
| 2020 | No Competition |
| 2019 | Amber Marshall |
Wilkinson Sword Winners
| Season | WINNER | REASON |
| 2023/24 | Ladies Masters Squad | National Champions O40 & O50 |
| 2022/23 | ||
| 2021/22 | Not Awarded | |
| 2020/21 | Not Awarded | Covid |
| 2019/20 | Not Awarded | Covid |
| 2018/19 | Not Awarded | |
| 2017/18 | Adrian Waller | Great achievement, silver medal in Commonwealth Games |
| 2016/17 | Mens O50 Team | National Champions |
| 2015/16 | Isobel Smith | Selected for England O50 and service to Herts Squash |
| 2014/15 | Ladies O50 County Team | National Champions |
| 2013/14 | Letchworth Squash Club | |
| 2012/13 | Broxbourne Squash Club | |
| 2011/12 | Not Awarded | |
| 2010/11 | Not Awarded | |
| 2009/10 | Not Awarded | |
| 2008/09 | Mens County 1st Team | National Champions |
| 2007/08 | Berkhamstead SC | |
| 2006/07 | Radlett Squash Club | Work with juniors and support of Herts Squash |
| 2005/06 | Cannons St Albans | For good results across the board and healthy junior section |
| 2004/05 | Bishops Stortford | Winning Div 1 and Herts Cup |
| 2003/04 | R3 Stevenage | Winning Division 1 for the first time |
| 2002/03 | Cannons St Albans | |
| 2001/02 | Haileybury Ladies Team | For fielding three teams in the league and coming 1st & 2nd |
| 2000/01 | Glaxo Smith Kline | |
| 1999/00 | Notel | |
| 1998/99 | Bishops Stortford SC | |
| 1997/98 | Berkhamstead SC | |
| 1996/97 | Herts Country Club | |
| 1995/96 | Herts Police | |
| 1994/95 | Broxbourne Squash Club | |
| 1993/94 | St Albans Squash Club | |
| 1992/93 | Herts Police | |
| 1991/92 | Radlett Squash Club | |
| 1990/91 | Herts Country Club | League achievements |
| 1989/90 | Woodside Country Club | |
