Tommy Hutton Challenge Cup
Presented in 1966 by Mr T Hutton as the season's points trophy for fast handicap races.
| Year | Helm | Crew | Class | Sail number | Boat name |
| 1966 | Mike Enderby | 505 | 1904 | Edelweiss | |
| 1967 | Mike Enderby | 505 | 1904 | Edelweiss | |
| 1968 | John Locke | 505 | 2726 | Miss Giving | |
| 1968 | --re-allocated in 1969 to 505 dinghies-- | ||||
| 1969 | John Locke | 505 | 3038 | Your 'Onour | |
| 1970 | Mike Enderby | 505 | 3504 | Aquila | |
| 1971 | S Raven | 505 | 3737 | Easy Rider | |
| 1972 | Not sailed | ||||
| 1973 | --re-allocated in 1973 for Lasers-- | ||||
| 1973 | A Jenkins | Laser | 3129 | Humbug | |
| 1974 | Chris Ellingham | Laser | 13366 | Piglet | |
| 1975 | Chris Ellingham | Laser | 30576 | Piglet II | |
| 1976 | Mike Powell | Laser | 41311 | Delicious II | |
| 1977 | Mike Powell | Laser | 41311 | Delicious II | |
| 1978 | Chris Ellingham | Laser | 54425 | Eeyore | |
| 1979 | Mike Powell | Laser | 54481 | Rockalaser Baby | |
| 1980 | Simon Bloxham | Laser | 81270 | Chocolate Brownie | |
| 1981 | Chris Treagust | Laser | 7297 | Imalone | |
| 1982 | Mike Powell | Laser | 88669 | Konstabel Els | |
| 1983 | Not sailed | ||||
| 1984 | Not sailed | ||||
| 1985 | --re-allocated in 1985 for the first-of-three points series-- | ||||
| 1985 | Ian Groom | Laser | 68961 | Flying Kipper | |
| 1986 | Roger Bleasby | Wayfarer | 6494 | Masquerade | |
| 1987 | Jonathan Townsend | Wayfarer | 6288 | Devon Pickle | |
| 1988 | Simon Pettit | Laser | 85064 | Lasepplin | |
| 1989 | Phil Poyner | Jill Poyner | Laser II | 7199 | |
| 1990 | Neil Mant | Laser | 122263 | Seek & Destroy | |
| 1991 | Jonathan Townsend | Albacore | 7508 | Force | |
| 1992 | Jonathan Townsend | Albacore | 7508 | Force | |
| 1993 | John Davis | Wayfarer | 981 | Rebecca | |
| 1994 | Phil Mant | Laser | 147810 | ||
| 1995 | Tim Weeden | Mel Millar | RS400 | 415 | |
| 1996 | John Davis | Wayfarer | 981 | Rebecca | |
| 1997 | Phil Mant | Laser | 154839 | ||
| 1998 | John Davis | Wayfarer | 981 | Rebecca | |
| 1999 | Neil Mant | Cath Mant | Buzz | 517 | Henry the Wasp |
| 2000 | Chris Treagust | Laser | 169989 | ||
| 2001 | Anthony Reeves | Laser | |||
| 2002 | Simon Townsend | Annie Porter | RS400 | 557 | |
| 2003 | Neil Mant | Laser | 155147 | Seek & Destroy | |
| 2004 | Neil Mant | Laser | 155147 | Seek & Destroy | |
| 2005 | Trevor Newley | Giles Bowman | Wayfarer | 998 | |
| 2006 | Neil Mant | Laser | 155147 | Seek & Destroy | |
| 2007 | Simon Pettit | Finn | 573 | ||
| 2008 | Simon Pettit | Finn | 573 | ||
| 2009 | Neil Mant | Laser | 7 | Seek & Destroy | |
| 2010 | Simon Townsend | Ben Townsend | National 12 | 3429 | Billy the Hoover |
| 2011 | Harry Derbyshire | John Derbyshire | RS200 | 1008 | |
| 2012 | Jonathan Townsend | Barbara Langford | 2000 | 21431 | Jambo II |
| 2013 | Phil Poyner | Jill Poyner | RS200 | 1004 | |
| 2014 | Max Jones | Laser | 204680 | ||
| 2015 | Sam Tweedle | Laser | 182262 | ||
| 2016 | Ben Oakley | Devoti D-Zero | 176 | ||
| 2017 | Ben Oakley | Devoti D-Zero | 176 | ||
| 2018 | Ben Oakley | Devoti D-Zero | 176 | ||
| 2019 | Patrick Bonner | Laser Radial | 216001 | ||
| 2020 | Not sailed - COVID-19 | ||||
| 2021 | Patrick Bonner | Laser | 216001 |