| East Divsion 1A | West Divsion 1A | |
| 2003 | Cowdrey | Bexley Third XI |
| 2004 | Cowdrey | Old Brockleians |
| 2005 | Minster | Bromley Town |
| 2006 | High Halstow | Gravesend |
| 2007 | Bapchild | Farningham |
| 2008 | Betteshanger Colliery Welfare | Tunbridge Wells Third XI |
| 2009 | Deal Victoria & Barns Close | Bickley Park Third XI |
| Premier Division | |
| 2010 | Cowdrey |
| 2011 | RACS |
| 2012 | Leeds & Broomfield |
| 2013 | Walmer |
| 2014 | Old Williamsonians |
| 2015 | Frindsbury |
| 2016 | High Halstow |
| 2017 | Staplehurst |
| 2018 | The Roebucks |
| 2019 | Borstal |
| Divsion 1 West | Divsion 1 East | |
| 2020 | LESSA Christ Church | Sibton Park |
| Division 1 Met/West | Division 1 Central | Division 1 East | |
| 2021 | Chislehurst & West Kent | Cobham | Sibton Park |
| 2022 | Simba | Gravesend | Mersham Sports |
Peter Hartland
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