SENIOR LEAGUE CUP
| Season | Winners | Runners-Up |
|---|---|---|
| 1966-67 | Bishops Stortford Swifts | Writtle |
| 1967-68 | Manor Athletic | Essex Police |
| 1968-69 | Basildon Town | Manor Athletic |
| 1969-70 | Chadwell Heath | Manor Athletic |
| 1970-71 | Billericay Town | Brentwood Athletic |
| 1971-72 | Chadwell Heath | Brentwood Athletic |
| 1972-73 | Runwell Hospital | Writtle |
| 1973-74 | Chadwell Heath | Essex Police |
| 1974-75 | Collier Row | Chadwell Heath |
| 1975-76 | Old Chelmsfordians | Burnham Ramblers |
| 1976-77 | Runwell Hospital | Collier Row |
| 1977-78 | Collier Row | Benfleet |
| 1978-79 | Takeley | Burnham Ramblers |
| 1979-80 | Runwell Hospital | Rayleigh Town |
| 1980-81 | Runwell Hospital | Rayleigh Town |
| 1981-82 | Herongate Athletic | Springfield |
| 1982-83 | Herongate Athletic | Takeley |
| 1983-84 | Benfleet | Cossor Sports |
| 1984-85 | Cossor Sports | Rayleigh Town |
| 1985-86 | Rochford Town | Rayleigh Town |
| 1986-87 | Bishops Stortford Swifts | Takeley |
| 1987-88 | Hullbridge Sports | Benfleet |
| 1988-89 | Upminster | Great Baddow Royals |
| 1989-90 | Concord Rangers | Kelvedon Hatch |
| 1990-91 | Old Chelmsfordians | Herongate Athletic |
| 1991-92 | Great Wakering | Kelvedon Hatch |
| 1992-93 | Kelvedon Hatch | Hatfield Peverel |
| 1993-94 | Writtle | Kelvedon Hatch |
| 1994-95 | Writtle | Standard (Harlow) |
| 1995-96 | Sandon Royals | Frenford Senior |
| 1996-97 | Danbury Trafford | Kelvedon Hatch |
| 1997-98 | Bishops Stortford Swifts | Takeley |
| 1998-99 | Bishops Stortford Swifts | Takeley |
| 1999-2000 | Frenford Senior | Nortel (Harlow) |
| 2000-01 | Sandon Royals | Frenford Senior |
| 2001-02 | Rayleigh Town | Broomfield |
| 2002-03 | White Ensign | Bishops Stortford Swifts |
| 2003-04 | White Ensign | Manford Way |
| 2004-05 | Shenfield A.F.C. | White Ensign |
| 2005-06 | Harold Wood Athletic | White Ensign |
| 2006-07 | Kelvedon Hatch | White Ensign |
| 2007-08 | Kelvedon Hatch | M & B Club |
| 2008-09 | Manford Way | M & B Club |
| 2009-10 | Westhamians | Hannakins Farm |
| 2010-11 | Rayleigh Town | Runwell Hopital |
| 2011-12 | Aldborough Athletic | Rayleigh Town |
| 2012-13 | Frenford Senior | Springfield |
| 2013-14 | Rayleigh Town | Southminster St. Leonards |
| 2014-15 | Kelvedon Hatch | Wadham Lodge |
| 2015-16 | Kelvedon Hatch | Manford Way |
| 2016-17 | Basildon Town | Kelvedon Hatch |
| 2017-18 | Frenford | Leigh Ramblers |
| 2018-19 | Bishops Stortford Swifts | Catholic United |
SENIOR CHALLENGE CUP
| Season | Winners | Runners-Up | |
|---|---|---|---|
| 1970-71 | Billericay Town | Chadwell Heath | |
| 1971-72 | Billericay Town | drew with | Brentwood Athletic |
| 1972-73 | Chadwell Heath | drew with | Sawbridgeworth |
| 1973-74 | Chadwell Heath | Runwell Hospital | |
| 1974-75 | Chadwell Heath | drew with | Benfleet |
| 1975-76 | Collier Row | Burnham Ramblers | |
| 1976-77 | Essex Police | Old Chelmsfordians | |
| 1977-78 | Collier Row | Runwell Hospital | |
| 1978-79 | Runwell Hospital | Benfleet | |
| 1979-80 | Rayleigh Town | Takeley | |
| 1980-81 | Essex Police | Runwell Hospital | |
| 1981-82 | Rayleigh Town | Herongate Athletic | |
| 1982-83 | Benfleet | Herongate Athletic | |
| 1983-84 | Springfield | drew with | Herongate Athletic |
| 1984-85 | Benfleet | Rayleigh Town | |
| 1985-86 | Rayleigh Town | Cossor Sports | |
| 1986-87 | Essex Police | Rochford Town | |
| 1987-88 | Essex Police | Bishops Stortford Swifts | |
| 1988-89 | Takeley | Hullbridge Sports | |
| 1989-90 | Benfleet | drew with | Upminster |
| 1990-91 | Concord Rangers | Rayleigh Town | |
| 1991-92 | Old Chelmsfordians | Herongate Athletic | |
| 1992-93 | Standard (Harlow) | drew with | Kelvedon Hatch |
| 1993-94 | Kelvedon Hatch | Standard (Harlow) | |
| 1994-95 | Writtle | Kelvedon Hatch | |
| 1995-96 | Writtle | Kelvedon Hatch | |
| 1996-97 | Kelvedon Hatch | Sandon Royals | |
| 1997-98 | Kelvedon Hatch | Danbury Trafford | |
| 1998-99 | Bishops Stortford Swifts | Frenford Senior | |
| 1999-2000 | Bishops Stortford Swifts | Rayleigh Town | |
| 2000-01 | Frenford Senior | Bishops Stortford Swifts | |
| 2001-02 | Rayleigh Town | Sandon Royals | |
| 2002-03 | Takeley | Rayleigh Town | |
| 2003-04 | White Ensign | Bishops Stortford Swifts | |
| 2004-05 | White Ensign | Manford Way | |
| 2005-06 | White Ensign | Shenfield A.F.C. | |
| 2006-07 | Frenford Senior | Harold Wood Athletic | |
| 2007-08 | White Ensign | Kelvedon Hatch | |
| 2008-09 | Kelvedon Hatch | White Ensign | |
| 2009-10 | Harold Wood Athletic | Manford Way | |
| 2010-11 | Harold Wood Athletic | Westhamians | |
| 2011-12 | Kelvedon Hatch | Rayleigh Town | |
| 2012-13 | Frenford Senior | Aldborough Athletic | |
| 2013-14 | Frenford Senior | Kelvedon Hatch | |
| 2014-15 | Southminster St. Leonards | Rayleigh Town | |
| 2015-16 | Kelvedon Hatch | Harold Wood Athletic | |
| 2016-17 | Kelvedon Hatch | Manford Way | |
| 2017-18 | Basildon Town | Springfield | |
| 2018-19 | Catholic United | Frenford Reserves | |
| 2019-20 | Bishops Stortford Swifts | Buckhurst Hill |
DENNY KING MEMORIAL CUP
| Season | Winners | Runners-Up |
|---|---|---|
| 1999-2000 | Manford Way | Barnston A.F.C. |
| 2000-01 | No Competition | |
| 2001-02 | Benfleet | Metpol Chigwell |
| 2002-03 | Benfleet | Linford Wanderers |
| 2003-04 | Bishops Stortford Swifts | Frenford Senior |
| 2004-05 | Manford Way | Springfield |
| 2005-06 | Epping | Ongar Town |
| 2006-07 | No Competition | |
| 2007-08 | Potter Street | Faces F.C. |
| 2008-09 | No Competition | |
| 2009-10 | Wadham Lodge | Epping |
| 2010-11 | Castle United | M & B Club |
| 2011-12 | M & B Club | Runwell Hospital |
| 2012-13 | No Competition |