| Winner | Runner-up | |
| Shepherd Neame Essex Cricket League Division Three | ||
| 1999 | Hutton | Upminster |
| 2000 | Harlow | Southend-on-Sea and Ekco Monarchs and Trojans |
| 2001 | Old Parkonians | Old Brentwoods |
| 2002 | Southend-on-Sea and Ekco Monarchs and Trojans | Ardleigh Green |
| 2003 | Hutton | Stanford-le-Hope |
| 2004 | Woodford Green | Epping |
| 2005 | Horndon-on-the-Hill | Basildon and Pitsea |
| 2006 | Stanford-le-Hope | Southend-on-Sea and Ekco Monarchs and Trojans |
| 2007 | Harold Wood | Old Southendian and Southchurch |
| 2008 | Billericay | Buckhurst Hill |
| 2009 | Benfleet | Stanford-le-Hope |
| 2010 | Walthamstow | Southend-on-Sea and Ekco Monarchs and Trojans |
| 2011 | Basildon and Pirsea | Belhus |
| 2012 | Billericay | Hutton |
| 2013 | West Essex | Westcliff-on-Sea |
| 2014 | Stanford-le-Hope | Harlow Town |
| 2015 | Old Southendian and Southchurch | Oakfield Parkonians |
| 2016 | Old Brentwoods | Basildon and Pitsea |
| 2017 | Leigh-on-Sea | Harlow Town |
| 2018 | Old Brentwoods | Benfleet |
| 2019 | Leigh-on-Sea | Westcliff-on-Sea |
David M Smith
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