| YEAR | BOAT No. | NAME | HELM | CREW |
| 2024 | 9 | Annamarie | Paddy Spink | Will Ellison |
| 2023 | 125 | Windspiel | Chris Gibbs | Maddie Gibbs |
| 2022 | 12 | Rock-a-Bye | Chris Gibbs | Tim Gibbs |
| 2021 | 125 | Windspiel | Chris Gibbs | Maddie Gibbs |
| 2020 | — | Not Sailed (covid) | — | Not Sailed |
| 2019 | 127 | Skybird | Adam Anthony | Charlie Andrews |
| 2018 | 125 | Windspiel | Will Gibbs | Chris Gibbs |
| 2017 | 125 | Windspiel | Will Gibbs | Chris Gibbs |
| 2016 | 9 | Annamarie | Paddy Spink | Roz Spink |
| 2015 | 125 | Windspiel | Chris Gibbs | Tim Gibbs |
| 2014 | 125 | Windspiel | Chris Gibbs | Tim Gibbs |
| 2013 | 125 | Windspiel | Chris Gibbs | Tim Gibbs |
| 2012 | 77 | Maid of Arnhem | Chris Gibbs | Tim Gibbs |
| 2011 | 125 | Windspiel | Chris Gibbs | Tim Gibbs |
| 2010 | 125 | Windspiel | Chris Gibbs | Tim Gibbs |
| 2009 | 125 | Windspiel | Chris Gibbs | Tim Gibbs |
| 2008 | 125 | Windspiel | Chris Gibbs | Tim Gibbs |
| 2007 | 125 | Windspiel | Chris Gibbs | Tim Gibbs |
| 2006 | 125 | Windspiel | Chris Gibbs | Tim Gibbs |
| 2005 | 77 | Maid of Arnhem | Chris Gibbs | Tim Gibbs |
| 2004 | 125 | Windspiel | Chris Gibbs | Tim Gibbs |
| 2003 | 75 | Cassiopia | Chris Bunn | Ian Tims |
| 2002 | 77 | Maid of Arnhem | Chris Gibbs | Tim Gibbs |
| 2001 | 77 | Maid of Arnhem | Chris Gibbs | Tim Gibbs |
| 2000 | 9 | Annamarie | Paddy Spink | John Ellison |
| 1999 | 9 | Annamarie | Paddy Spink | John Ellison |
| 1998 | 9 | Annamarie | Paddy Spink | John Ellison |
| 1997 | 9 | Annamarie | Paddy Spink | John Ellison |
| 1996 | 12 | Rock-A-Bye | James Case | Harvey Wynne |
| 1995 | 9 | Annamarie | Paddy Spink | John Ellison |
| 1994 | 9 | Annamarie | Paddy Spink | John Ellison |
| 1993 | 129 | Madrigal | Richard Cracknell | Rob Wynne |
| 1992 | 116 | Northern Lights | Peter Scillitoe | Terry Norton |
| 1991 | 129 | Inca | Richard Cracknell | De Nudds |
| 1990 | 77 | Maid of Arnhem | Chris Gibbs | Tim Gibbs |
| 1989 | 129 | Inca | Richard Cracknell | De Nudds |
| 1988 | 12 | Rock – A – Bye | Richard Cracknell | De Nudds |
| 1987 | 125 | Windspiel | Richard Cracknell | De Nudds |
| 1986 | 78 | Redwing | Gary Anthony | Alan Coe |
| 1985 | 95 | Tern III | Paddy Spink | John Ellison |
| 1984 | 12 | Rock – A – Bye | James Case | Tim Gibbs |
| 1983 | 127 | Skybird | Tony Barnham | Jasper Barnham |
| 1982 | 106 | Miranda | Richard Cracknell | De Nudds |
| 1981 | 111 | Southern Cross | Matt Hall-Smith | Andy Maxey |
| 1980 | 116 | Northern Lights | Peter Scillitioe | Terry Norton |
| 1979 | 116 | Northern Lights | Peter Scillitioe | Terry Norton |
| 1978 | 76 | Annabella | Tony Barnham | David Emerson |
| 1977 | 101 | Sea Witch | Richard Cracknell | De Nudds |
| 1976 | 76 | Annabella | Tony Barnham | David Emerson |
| 1975 | 101 | Sea Witch | Richard Cracknell | De Nudds |
| 1974 | 75 | Cassiopia | Ronnie Scoles | Willy Outred |
| 1973 | 101 | Sea Witch | Richard Cracknell | De Nudds |
| 1972 | 101 | Sea Witch | Richard Cracknell | De Nudds |
| 1971 | 100 | Whimbrel | Brian Grimes | John Balls |
| 1970 | 100 | Whimbrel | Brian Grimes | Roger Richardson |
| 1969 | 73 | Tern II | Tommy Thomas | David Hudson |
| 1968 | 100 | Whimbrel | Brian Grimes | |
| 1967 | 100 | Whimbrel | Brian Grimes | |
| 1966 | 75 | Cassiopia | Ronnie Scoles | Willy Outred |
| 1965 / 64 | Not Sailed | |||
| 1963 | 70 | Patience | Tommy Thomas | |
| 1962 | 100 | Whimbrel | Tony Barnham | Janet Barnham |
| 1961 } | 75 | Cassiopia | } Ronnie Scoles | } Joint |
| 1961 } | 100 | Whimbrel | } Tony Barnham | } Winners |
| 1960 | 113 | Fortuna | Janet Sanderson | Keith Sanderson |
| 1959 | 110 | Pitzi | H S N Simms-Adams | |
| 1958 | 116 | Northern Lights | J E A Lambert | |
| 1957 | 63 | Chuckles | Gerald Bell | |
| 1956 | 34 | Ynys | Jasper Blackall | |
| 1955 | 119 | Southern Sun | Charles Currey | Tony Warrilow |
| 1954 | 119 | Southern Sun | Charles Currey | Tony Warrilow |
| 1953 | 117 | Frolic | R J Garnham | |
| 1952 | O T Atkins | |||
| 1951 } | 85 | Marlborough | } Mrs J Heriot | } Joint |
| 1951 } | 50 | Maid of Amsterdam | } W J Borthwick | } Winners |
| 1950 | 34 | Ynys | H F Blackall | |
| 1949 | 63 | Chuckles | Charles Currey | |
| 1947 – 48 | Not Sailed | |||
| 1946 | 26 | Cutty Sark | E S Dawes | |
| 1939 – 45 | War Years | Not Sailed | ||
| 1938 | Sancho Panza | B Westwood | ||
| 1937 | Sancho Panza | Beecher Moore | ||
| 1936 | 17 | Taeping | W H Ogilvie | |
| 1935 | Thermopylae | T A Mason | ||
| 1934 | Sancho Panza | W Rendell | ||
| 1933 | 24 | Samuel Plimsoll | Miss J Joy |