| Year | Division | Winners | Runners Up |
|---|---|---|---|
| 2023-2024 | Premiership | Foresters A | TJs A |
| 2023-2024 | Division One | Spots & Stripes A | TJs B |
| 2022-2023 | Premiership | TJ's A | Elephant's Head A |
| 2022-2023 | Division One | Rose AA | Spots & Stripes A |
| 2021-2022 | Premiership | Bat & Ball A | Spots & Stripes X |
| 2021-2022 | Division One | Viewpoint A | Viewpoint B |
| 2019-2020 | Premiership | Elephants Head X | Peacock A |
| 2019-2020 | Division One | Edinburgh Castle | Painters Ash |
| 2019-2020 | Division Two | Pavillion B | The Wheatsheaf |
| 2017-2018 | Premiership | Bat & Ball A | The Rose A |
| 2017-2018 | Divison One | Viewpoint | Pelham Arms A |
| 2017-2018 | Division Two | The Wheatsheaf | The Cricketers |
| 2016-2017 | Premiership | The Rose A | Prince Albert A |
| 2016-2017 | Divison One | Spots & Stripes D | Villager A |
| 2016-2017 | Division Two | Ascot | Pelham Arms B |
| 2015-2016 | Premiership | Prince Albert A | The Peacock |
| 2015-2016 | Divison One | Spots & Stripes C | Pavilion |
| 2015-2016 | Division Two | Painters Ash | Pelham Arms B |
| 2014-2015 | Premiership | New Inn A | The Peacock |
| 2014-2015 | Divison One | Pelham Arms | The Rose A |
| 2014-2015 | Division Two | Spots & Stripes C | Foresters Arms B |
| 2013-2014 | Premiership and One | Bat and Ball A | Prince of Orange A |
| 2013-2014 | Divison Two and Three | The Wheatsheaf | Elephants Head B |
| 2012-2013 | Premiership and One | Prince Albert A | Battle Of Britain |
| 2012-2013 | Divison Two and Three | TJ’s | Foresters B |
| 2011-2012 | Premiership and One | Bat & Ball A | Bat & Ball B |
| 2011-2012 | Divison Two and Three | Ascot Arms C | Stork at Rest |
| 2010-2011 | Premiership and One | Pelham Arms | Peacock |
| 2010-2011 | Divison Two and Three | Prince of Orange A | Man of Kent |
| 2009-2010 | Premiership and One | Bat & Ball A | Spots & Stripes A |
| 2009-2010 | Divison Two and Three | Regan?s Bar | Edinburgh Castle |
| 2008-2009 | Premiership and One | Bat & Ball A | Peacock |
| 2008-2009 | Divison Two and Three | Foresters Arms | Spots & Stripes B |
| 2007-2008 | Premiership and One | Bat & Ball A | George & Dragon |
| 2007-2008 | Divison Two and Three | Spots & Stripes B | Pelham Arms B |
| 2006-2007 | Premiership and One | Bat & Ball A | Peacock A |
| 2006-2007 | Divison Two and Three | Spots & Stripes B | Pelham Arms B |
| 2005-2006 | Premiership and One | Peacock A | Dover Castle A |
| 2005-2006 | Divison Two and Three | Waterloo A | Viewpoint |
| 2004-2005 | Premiership and One | Bat & Ball A | Prince Albert A |
| 2004-2005 | Divison Two and Three | Painters Ash B | George & Dragon |
| 2003-2004 | Premiership and One | Prince Albert A | Pelham Arms A |
| 2003-2004 | Divison Two and Three | Villager | Dover Castle B |
| 2002-2003 | Premiership | Prince Albert A | Pelham Arms A |
| 2002-2003 | Divison One and Two | ||
| 2002-2003 | Divison One and Four | Peacock A | Peacock B |
| 2002-2003 | Divison Three and Five | ||
| 2001-2002 | Premiership | Prince Albert A | Bat & Ball A |
| 2001-2002 | Divison One and Two | ||
| 2001-2002 | Divison One and Four | Westcourt | Foresters |
| 2001-2002 | Divison Three and Five | ||
| 2000-2001 | Premiership | Prince Albert A | Peacock A |
| 2000-2001 | Divison One and Two | Pelham Arms | Bat & Ball B |
| 2000-2001 | Divison One and Four | ||
| 2000-2001 | Divison Three and Five | Dover Castle | Clarence B |