| Winner | Runner-up | |
| Shepherd Neame Essex Cricket League Premier Division | ||
| 1999 | Fives and Heronians | Saffron Walden |
| 2000 | Wanstead | Saffron Walden |
| 2001 | Saffron Walden | Wanstead |
| 2002 | Gidea Park and Romford | Wanstead |
| 2003 | Saffron Walden | Gidea Park and Romford |
| 2004 | Saffron Walden | Wanstead |
| 2005 | Saffron Walden | Hainault and Clayhall |
| 2006 | Hainault and Clayhall | Saffron Walden |
| 2007 | Ardleigh Green | Wanstead |
| 2008 | Wanstead | Ardleigh Green |
| 2009 | Brentwood | Wanstead |
| 2010 | Brentwood | Wanstead |
| 2011 | Brentwood | Wanstead and Snaresbrook |
| 2012 | Wanstead and Snaresbrook | Chelmsford |
| 2013 | Wanstead and Snaresbrook | Brentwood |
| 2014 | Chingford | Wanstead and Snaresbrook |
| 2015 | Chelmsford | Brentwood |
| 2016 | Wanstead and Snaresbrook | Brentwood |
| 2017 | Chelmsford | Wanstead and Snaresbrook |
| 2018 | Hornchurch | Wanstead and Snaresbrook |
| 2019 | Brentwood | Wanstead and Snaresbrook |
David M Smith
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