| Season |
Winners |
Runners-up |
| 2005-06 |
Felixstowe & Walton United |
AFC Sudbury |
| 2006-07 |
Stanway Rovers |
Bury Town |
| 2007-08 |
Haverhill Rovers |
Walsham Le Willows |
| 2008-09 |
Lowestoft Town |
Haverhill Rovers |
| 2009-10 |
Lowestoft Town |
Hadleigh United |
| 2010-11 |
Braintree Town |
Lowestoft Town |
| 2011-12 |
Braintree Town |
Gorleston |
| 2012-13 |
Maldon & Tiptree |
Brightlingsea Regent |
| 2013-14 |
Felixstowe & Walton United |
Brantham Athletic |
| 2014-15 |
Witham Town |
Brightlingsea Regent |
| 2015-16 |
Witham Town |
Hadleigh United |
| 2016-17 |
Stanway Rovers |
Woodbridge Town |
| 2017-18 |
Halstead Town |
Witham Town |
| Division One |
|
|
| 2012-13 |
Brantham Athletic |
Felixstowe & Walton United |
| 2013-14 |
Hadleigh United |
Halstead Town |
| 2014-15 |
Saffron Walden Town |
Wivenhoe Town |
