Men’s Singles
The Bob Cole Cup
| 1965-66 R. King (Burnham Sports Club A) | 1993-94 S. Edwards (Fambridge) |
| 1966-67 M. Robinson (Southminster A) | 1994-95 S. Woods (Cold Norton) |
| 1967-68 M. Robinson (Southminster A) | 1995-96 P. Ballard (Fambridge) |
| 1968-69 D. Lomas (Burnham Sports Club A) | 1996-97 H. Innes (Hullbridge) |
| 1969-70 M. Robinson (Southminster A) | 1997-98 R. Savill (Hullbridge) |
| 1970-71 S. Whiteley (Maldon Wanderers) | 1998-99 P. Ballard (Fambridge) |
| 1971-72 S. Whiteley (Maldon Wanderers) | 1999-00 G. Reeves (Mapledene) |
| 1972-73 P. Orris (Maldon Wanderers) | 2000-01 G. Reeves (Mapledene) |
| 1973-74 C. Barrell (Mayland) | 2001-02 G. Reeves (Mapledene) |
| 1974-75 S. Greep (Maldon Wanderers) | 2002-03 P. Ballard (Fambridge) |
| 1975-76 D. Newman (MET Wanderers) | 2003-04 K. Read (Mapledene) |
| 1976-77 M. Speight (Mayland) | 2004-05 K. Read (Mapledene) |
| 1977-78 M. Speight (Mayland) | 2005-06 K. Read (Mapledene) |
| 1978-79 G. Booth (South Woodham) | 2006-07 G. Reeves (Mapledene) |
| 1979-80 R. Lang (Maldon Wanderers) | 2007-08 P. Ballard (Fambridge) |
| 1980-81 S. Whiteley (Maldon Wanderers) | 2008-09 M. Jovic (Fambridge) |
| 1981-82 T. Dowsett (East Hanningfield) | 2009-10 S. Gibbs (Mapledene) |
| 1982-83 S. Tilson (East Hanningfield) | 2010-11 S. Gibbs (Mapledene) |
| 1983-84 S. Whiteley (Maldon Wanderers) | 2011-12 K. Read (Mapledene) |
| 1984-85 R. Lang (Maldon Wanderers) | 2012-13 J. Monk (Mapledene) |
| 1985-86 M. Speight (CEGB) | 2013-14 D. Taylor (Cold Norton) |
| 1986-87 M. Speight (CEGB) | 2014-15 D. Taylor (Cold Norton) |
| 1987-88 C. Jacob (East Hanningfield) | 2015-16 T. Halling (Mapledene) |
| 1988-89 P. Ballard (Fambridge) | 2016-17 R. Seddon (Mapledene) |
| 1989-90 D. Newman (Maldon) | 2017-18 D. Taylor (Cold Norton) |
| 1990-91 M. Stones (Fambridge) | 2018-19 D. Young (West Maldon) |
| 1991-92 M. Stones (Fambridge) | |
| 1992-93 S. Woods (Cold Norton) |
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