Bailey Cup
Presented in 1957 by EJ Bailey Esq, as the trophy for a handicap race in the Junior Regatta. Re-allocated in 1992 as a trophy for Laser IIs in the Club regatta (not restricted to juniors). in 2013, re-allocated to a short course race for juniors.
| Year | Helm | Crew | Class | Sail number | Boat name |
| 1957 | J Pengelly | Firefly | 35 | Blodwyn | |
| 1958 | Not sailed | ||||
| 1959 | MS Yden, BSC | Eleven Plus | 27 | ||
| 1960 | JA Bibby, BSC | Swiz | |||
| 1961 | JRC Peters | Wild Cat | 274 | Minx | |
| 1962 | DA Sadler, BSC | Albacore | 1163 | Whirlwind | |
| 1963 | T Phillips, Tudor SC | Fireball | 64 | ||
| 1964 | RG Keyworth, Tudor SC | Fleetwind | 298 | Jaie | |
| 1965 | Not sailed | ||||
| 1966 | AN Pusinelli | Enterprise | 8557 | Dog Dingo | |
| 1967 | Diana Beale, BSC | Gull | 916 | Gulliver | |
| 1968 | MTF Briggs, BSC | Gull | 153 | Mon Amie | |
| 1969 | M Marsden, DQSC | Gull | 1184 | Rosie | |
| 1970 | GR Lewis | Wayfarer | 74 | Eliza | |
| 1971 | MK Simpkin | Enterprise | 4337 | Aquaphobia | |
| 1972 | GR Lewis | Wayfarer | 74 | Eliza | |
| 1973 | PG Bannister, LSC | Moth | 3401 | Strider | |
| 1974 | RJ Strange | Solo | 1894 | Ardue | |
| 1975 | SN Ray, MRSC | Gull | 1939 | Slick Dick | |
| 1976 | Marcus Lawson | Gull | 153 | Mon Amie | |
| 1977 | C Morgan, HISC | Cadet | 6194 | Helium II | |
| 1978 | Ben Oakley | Topper | 5977 | Mind Boggler | |
| 1979 | Liz Bowman | Pacer | 1703 | Ex Libris | |
| 1980 | A Morse, ESSC | Pacer | 137 | Dolly Rocker | |
| 1981 | Not sailed | ||||
| 1982 | Not sailed | ||||
| 1983 | Not sailed | ||||
| 1984 | Not sailed | ||||
| 1985 | Not sailed | ||||
| 1986 | Not sailed | ||||
| 1987 | Not sailed | ||||
| 1988 | J Fildes, DQSC | ||||
| 1989 | J Fildes, DQSC | Mirror | 55579 | Yas-Ta-Bum-Pit | |
| 1990 | J Fildes, DQSC | ||||
| 1991 | Not sailed | ||||
| 1992 | Joe Burnie | Laser II | 8306 | ||
| 1993 | Marcus Lawson | Anne Lawson | Laser II | 8406 | Laysawake Too |
| 1994 | Not sailed | ||||
| 1995 | Not sailed | ||||
| 1996 | Not sailed | ||||
| 1997 | Re-allocated to Short course race | ||||
| 1998 | C Wade | Topper | 40368 | ||
| 1999 | Not sailed | ||||
| 2000 | Margaret Jay | Scow | 626 | ||
| 2001 | Margaret Jay | Scow | 626 | ||
| 2002 | Susan Stewart-Fitzroy | Scow | 627 | ||
| 2003 | G Ellis | RS Feva XL | 419 | ||
| 2004 | Izzy Allerston | Optimist | 5270 | ||
| 2005 | Tom Durham | Topper | 44586 | ||
| 2006 | Jess Derbyshire | RS Feva XL | |||
| 2007 | Not sailed | ||||
| 2008 | David Patterson | Laser | 189330 | ||
| 2009 | Sam Tweedle | Optimist | |||
| 2010 | Bruce Ramsey | ||||
| 2011 | Jemima Lawson | Laser 4.7 | |||
| 2012 | Not sailed | ||||
| 2013 | Not sailed | ||||
| 2014 | Henry Chandler | Optimist | |||
| 2015 | Sam Thomson | Optimist | |||
| 2016 | Ben Millard (joint winner) | RS Tera Sport | |||
| 2016 | Henry Chandler (joint winner) | Optimist | |||
| 2017 | Patrick Bonner | Laser 4.7 | |||
| 2018 | Oscar Pitman | Optimist | |||
| 2019 | Not sailed - weather | ||||
| 2020 | Not sailed - COVID-19 | ||||
| 2021 |