The Chester Cup is a teams-of-four competition. Entries are divided into two divisions with the leading teams playing off in semi-finals and a final.
| 1967-68 | D V Booker, J H Freeman, R Perrin & L Salmon |
| 1968-69 | G H Edwardson, D P Hoskins, Mrs C O Priday, R C Rawcliffe, Mrs R C Rawcliffe & R R Scott |
| 1969-70 | Mrs D Smythies, D J Wheeler, ES Staveley & Mrs ES Staveley |
| 1970-71 | Mrs D Smythies, D J Wheeler, ES Staveley & Mrs E S Staveley |
| 1971-72 | R G Beck, Mrs RG Beck, Mrs R Bloch & E F Bowtell |
| 1972-73 | E S Staveley, Mrs E S Staveley, Mrs P Smythies & D J Wheeler |
| 1973-74 | R G Beck, Mrs R G Beck, Mrs R Bloch & E F Bowtell |
| 1974-75 | R C Rawcliffe, Mrs R C Rawcliffe, G H Edwardson & C Juneman |
| 1975-76 | Sir N Chester, R Van Noorden, F G Constable & K Harrap |
| 1976-77 | J Rudolf, Mrs J Rudolf, P M Hayes & Mrs R Bloch |
| 1977-78 | B A Claridge, Mrs B A Claridge, Miss D Nicholson, R Procter & E J Rudolf |
| 1978-79 | B A Claridge, Mrs B A Claridge, Miss D Nicholson, Mrs M Day & K Harrap |
| 1979-80 | B A Claridge, Mrs B A Claridge, Miss D Nicholson, Mrs M Day, J Williams & D Woodwark |
| 1980-81 | R Kilby, Mrs K Kilby, M Dancer & D Southcombe |
| 1981-82 | B A Claridge, Mrs B A Claridge, Mrs M Day, J Williams, M Robinson & R Procter |
| 1982-83 | R Pickard, Mrs P Smythies, Mrs J Godfrey & Mrs R Horne |
| 1983-84 | R Whittacker, G Towns, P Burton & M Renshaw |
| 1984-85 | B A Claridge, Mrs B A Claridge, J Williams, N Perceval-Price, D Maisonnier & P Briggs |
| 1985-86 | G T Cornell, D S Wallace, R C Fedrick, S C Brown, M Q Choyce & D Lockett |
| 1986-87 | S C Brown, D S Wallace, D Barker & D Walker |
| 1987-88 | B A Claridge , Mrs A J Claridge, J R T Williams, N Perceval-Price, R C Procter & Mrs M Day |
| 1988-89 | S C Brown, J R Bolgar, Mrs M Day & A Badiani |
| 1989-90 | Mrs M E Day, S C Brown, Mrs R Bavin & A Badiani |
| 1990-91 | Mrs A J Claridge, B A Claridge, G Liggins, P Lamford, J Williams & R Procter |
| 1991-92 | J R T Williams, B A Claridge, Mrs A J Claridge, R C Procter, G Liggins & P Lamford |
| 1992-93 | J R T Williams, B A Claridge, Mrs A J Claridge & R C Procter |
| 1993-94 | Mrs M Day, A Badiani, M H Goldsmith & C N Smith |
| 1994-95 | Mrs M Day, Mrs G Lonsdale, Mrs N Davenport, Dr H Lawton Smith & M H Goldsmith |
| 1995-96 | D Southcombe, M Dancer, Mrs J Brown, I Brooks, R Kilby & J Cullen |
| 1996-97 | Mrs M Day, Mrs G Lonsdale, Mrs N Davenport & Dr H Lawton Smith |
| 1997-98 | C N Smith, M Goldsmith, D Talbot & Mrs K Talbot |
| 1998-99 | Mrs M Day, Mrs G Lonsdale, R Lonsdale, Dr H Lawton Smith, Mrs P Rhodes-Fisher & N Wilkes |
| 1999-00 | C N Smith, M Goldsmith, D Talbot & Mrs K Talbot |
| 2000-01 | Mrs A Jackson, P Jackson, Mrs S Tulip, J Clifford & C Keep |
| 2001-02 | N Smith, R Procter, D Talbot & K Talbot |
| 2002-03 | Mrs G Lonsdale, Mrs P Rhodes-Fisher, N Wilkes, M Brown & C Keep |
| 2003-04 | D Talbot, Mrs K Talbot, R Procter & N Smith |
| 2004-05 | Mrs G Lonsdale, N Wilkes, M Brown, J Slater & C Keep |
| 2005-06 | D Talbot, Mrs K Talbot, N Smith, R Procter, S Noble & R Lonsdale |
| 2006-07 | D Talbot, Mrs K Talbot, N Smith, R Procter & C Cooper |
| 2007-08 | C Cooper, Ms B Youngs, M Clark, L Porter, I Angus & E Jones |
| 2008-09 | Mrs A Jackson, P Jackson, C Jones & M Currie |
| 2009-10 | Mike Brown, Gillian Lonsdale, Clive Keep, John Slater & Nigel Wilkes |
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