| Year | Winners | Runners-up |
| 2024 | Chatham Endurance | Chatham Ark Royal |
| 2023 | Chatham Javelin | Cliffe Woods 1 |
| 2022 | Cliffe Woods 1 | Sturdee 1 |
| 2021 | No competition - Covid | |
| 2020 | Chatham Ark Royal | Chatham Belfast |
| 2019 | Rainham 5 | Upnor A |
| 2018 | Chatham Gannet | Anchorians 3 |
| 2017 | Anchorians 3 | Upnor A |
| 2016 | Howard 3 | Anchorians 1 |
| 2015 | Howard 4 | Howard 5 |
| 2014 | Anchorians II | Howard 2 |
| 2013 | Howard IX | Rainham 83 I |
| 2012 | Chatham Endurance | Sturdee VI |
| 2011 | Chatham Cumberland | Luton Invicta II |
| 2010 | Sturdee V | Chatham Cumberland |
| 2009 | Sturdee II | Sturdee VII |
| 2008 | Howard 7 | Anchorians II |
| 2007 | Boxley II | Rainham 83 V |
| 2006 | Howard 9 | Howard 3 |
| 2005 | Rainham 83 XI | Chatham Endurance |
| 2004 | Rainham 83 VII | Sisalkraft II |
| 2003 | Lloyds | Sisalkraft II |
| 2002 | Anchorians I | Rainham 83 IV |
| 2001 | Civil Service I | Chatham V |
| 2000 | Rainham 83 IX | Sturdee VI |
| 1999 | B T Engineers II | Rainham 83 VIII |
| 1998 | Rosedale | Lordswood II |
| 1997 | Co-op IV | Parkwood II |
| 1996 | Medway Police I | Parkwood II |
| 1995 | Rainham 83 IV | Medway Water |
| 1994 | ASE II | Nomads VII |
| 1993 | ASE II | Rainham 83 VI |
| 1992 | Medway Nalgo | Walderslade Vikings II |
| 1991 | ASE II | Oasthouse IV |
| 1990 | Cliffe Woods I | Rugby Cement II |
| 1989 | Police II | Lordswood III |
| 1988 | Co-op IV | Rugby Cement II |
| 1987 | Wyvern II | Lloyds I |
| 1986 | R & W ‘M’ | Wigmore 79 VIII |
| 1985 | Wyvern | Nomads I |
| 1984 | R & W ‘O’ | Boxley III |
| 1983 | R & W ‘A’ | Rugby Cement V |
| 1982 | Wigmore 79 V | Naval Base III |
| 1981 | Walderslade Vikings I | Oasthouse III |
| 1980 | Rugby Cement I | Goodies V |
| 1979 | Hoboes II | Unity II |
| 1978 | Icepol | Elliots III |
| 1977 | Hoboes III | Sturdee I |
| 1976 | Sturdee I | Sturdee II |
| 1975 | CTR Bowaters I | Meadowside I |
| 1974 | Sturdee I | Weapons I |
| 1973 | Sturdee I | Hobourn Sports |
| 1972 | Forester II | Sturdee I |
| 1971 | Medway Engineers I | Sturdee II |
| 1970 | Conservatives | Medway Electric |
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