| 1985-86 | Chelmsford City | Billericay Town | 3-0 (agg.) |
| 1986-87 | Dagenham | Southend United | 2-1 |
| 1987-88 | Grays Athletic | Leytonstone-Ilford | 1-0 |
| 1988-89 | Chelmsford City | Grays Athletic | 3-2 |
| 1989-90 | Barking | Southend United | 1-1, 4-0 pens(?) |
| 1990-91 | Southend United | Leyton Orient | 1-1, 3-2 pens |
| 1991-92 | Redbridge Forest | Chelmsford City | 3-0 |
| 1992-93 | Chelmsford City | Wivenhoe Town | 1-0 |
| 1993-94 | Grays Athletic | Billericay Town | 1-0 |
| 1994-95 | Grays Athletic | Billericay Town | 1-0 |
| 1995-96 | Braintree Town | Billericay Town | 2-1 |
| 1996-97 | Southend United | Braintree Town | 2-1 |
| 1997-98 | Dagenham & Redbridge | Purfleet | 2-1 |
| 1998-99 | Canvey Island | Leyton Orient | 2-1 |
| 1999-00 | Canvey Island | Purfleet | 2-0 |
| 2000-01 | Dagenham & Redbridge | Canvey Island | 2-2, 5-3 pens |
| 2001-02 | Canvey Island | Dagenham & Redbridge | 6-1 |
| 2002-03 | Chelmsford City | Aveley | 5-0 |
| 2003-04 | Thurrock | Aveley | 3-1 |
| 2004-05 | Thurrock | Halstead Town | 1-0 |
| 2005-06 | Waltham Forest | Awarded trophy |
Please credit the F.C.H.D. when using this information elsewhere