| Season | Winners | Runners-up |
| 2024-25 | Framlingham Town | Brantham Athletic |
| 2023-24 | Stowmarket Town | HalsteadTown |
| 2022-23 | Halstead Town | Framlingham Town |
| 2018-19 | Halstead Town | Walsham le Willows |
| 2017-18 | Saffron Walden Town | Stowmarket Town |
| 2016-17 | Stanway Rovers | Walsham le Willows |
| 2015-16 | Brightlingsea Regent | Witham Town |
| 2014-15 | Lowestoft Town | Brightlingsea Regent |
| 2013-14 | Walsham le Willows | Halstead Town |
| 2012-13 | Brantham Athletic | Walsham Le Willows |
| 2011-12 | Gorleston | AFC Sudbury |
| 2010-11 | Braintree Town | Lowestoft Town |
| 2009-10 | Halstead Town | Gorleston |
| 2008-09 | AFC Sudbury | Tiptree United |
| 2007-08 | Ipswich Wanderers | Wroxham |
| 2006-07 | Wroxham | Tiptree United |
| 2005-06 | Bury Town | Wroxham |
| 2004-05 | Histon A | Mildenhall Town |
| 2003-04 | Bury Town | Tiptree United |
| 2002-03 | Mildenhall Town | Whitton United |
| 2001-02 | Wroxham | Bury Town |
| 2000-01 | Wroxham | Stowmarket Town |
Framlingham Town Under 23s – Chell Trophy Winners 2024/25 (picture by Dean Warner)
| Season | Winners | Runners-up |
| 2024-25 | Framlingham Town | Brantham Athletic |
| 2023-24 2022-23 |
Stowmarket Town Halstead Town |
Halstead Town Framlingham Town |
| 2018-19 | Halstead Town | Walsham le Willows |
| 2017-18 | Saffron Walden Town | Stowmarket Town |
| 2016-17 | Stanway Rovers | Walsham le Willows |
| 2015-16 | Brightlingsea Regent | Witham Town |
| 2014-15 | Lowestoft Town | Brightlingsea Regent |
| 2013-14 | Walsham le Willows | Halstead Town |
| 2012-13 | Brantham Athletic | Walsham Le Willows |
| 2011-12 | Gorleston | AFC Sudbury |
| 2010-11 | Braintree Town | Lowestoft Town |
| 2009-10 | Halstead Town | Gorleston |
| 2008-09 | AFC Sudbury | Tiptree United |
| 2007-08 | Ipswich Wanderers | Wroxham |
| 2006-07 | Wroxham | Tiptree United |
| 2005-06 | Bury Town | Wroxham |
| 2004-05 | Histon A | Mildenhall Town |
| 2003-04 | Bury Town | Tiptree United |
| 2002-03 | Mildenhall Town | Whitton United |
| 2001-02 | Wroxham | Bury Town |
| 2000-01 | Wroxham | Stowmarket Town |