| Inter-Divisional Cup Senior |
| Year | Winner | Runner-Up | Referee | Score |
| 1967-1968 | Greaves and Thomas | St Hare | T Lewis | n/a |
| 1968-1969 | Greaves and Thomas | Stortford Cioltsd | K Tate | 2-1 |
| 1969-1970 | Greaves and Thomas | Waterhouse | C Pooley | 2-0 |
| 1970-1971 | Nettleswell Dynamo | Greaves and Thomas | T Lewis | 2-1 |
| 1971-1972 | Nettleswell Dynamo | Granville | W Bruty | 4-1 |
| 1972-1973 | Nettleswell Dynamo | Pools United | K Miller | 2-1 (ET) |
| 1973-1974 | Pools United | Tye Green | E Natley | 5-0 |
| 1974-1975 | Pools United | St Hare | J Moules | 3-1 |
| 1975-1976 | Epping Foresr | Sawbridgeworth | A King | 4-0 |
| 1976-1977 | Pools United | Bulmer | P Maher | 3-2 (ET) |
| 1977-1978 | Phoenix Dynamo | Marquis of Granby | A Winn | 4-0 |
| 1978-1979 | Pools United | PhoenixAthletic | W Wiseman | 2-2/ 4-3 pens |
| 1979-1980 | Phoenix Athletic | Burnt Mill Staff | A Danskin | 1-1/ 4-2 pens |
| 1980-1981 | Phoenix Athletic | Pools Uniyted | A Winn | 1-0 |
| 1981-1982 | Pools United | Carey | N/A | 1-0 |
| 1982-1983 | Phoenix | Burnt Mill Staff | J Mayhew | 1-0 |
| 1983-1984 | Pools United | Phoenix Athletic | A Townsend | 1-0 |
| 1984-1985 | Marquis Sports | Carey Athletic | R Lund/A Townsend | 1-1/ 1-0 pens |
| 1985-1986 | Burnt Mill Staff | Lindsey Street | J Mayhew | 2-1 |
| 1986-1987 | Burnt Mill Staff | Phoenix | A Mann | 1-0 |
| 1987-1988 | Pools | United Glass Res | M Holnes | 1-0 |
| 1988-1989 | Drinker Moth | Burnt Mill Staff | J Norbury | 1-0 |
| 1989-1990 | Harlow Rangers | Marquis Sports | M Holmes | 3-2 |
| 1990-1991 | Phoenix Athletic | Pools United | A Stokes | 0-0/ 4-2 pens |
| 1991-1992 | Pools United | Northbrooks CA | R Brayne | 5-0 |
| 1992-1993 | UG Sports | Marquis Sports | F Fox | 2-0 |
| 1993-1994 | COMPETITION CHANGED OVER TO | HARLOW AND DISTRICT FOOTBALL | LEAGUE | CUP |
| 1993-1994 | Cossor Swifts | Dorstel | K Fussell | 2-1 |
| 1994-1995 | Maypole Athletic | Marquis Sports | H Newnham | 4-2 |
| 1995-1996 | Marquis Sports | Dorstel | G Garner | 1-0 |
| 1996-1997 | Maypole Athletic | Town Link | M Cooper | 2-2 (ET) |
| 1997-1998 | Matching United | Maypole Athletic | M Laforce | 2-1 |
| 1998-1999 | Marquis Sports | Grangers | J Hawkins | 4-0 |
| 1999-2000 | Maypole Athletic | Marquis Sports | S Williamson | 3-0 |
| 2000-2001 | COMPETITION | CANCELLED | BAD | WEATHER |
| 2001-2002 | Marquis Sports | G.P.C.A | A Tyne | 4-3 (ET) |
| 2002-2003 | Marquis Sports | Risden Wood | L Dorling | 3-3 (ET) 5-4 pens |
| 2003-2004 | GPCA | GPCA Reserves | | |
| 2004-2005 | GPCA | Maypole Athletic Reserves | | |
| 2005-2006 | Marquis Sports | Maypole Athletic | | 1-0 |
| 2006-2007 | Rouge Lyon | GPCA | | |
| 2007-2008 | Parndon Royals | GPCA | | 2-0 |