| Year | Helm | Dragon | Crew, Location |
|---|---|---|---|
| 2023 | Graham Bailey | Bluebottle | Julia Bailey, Katie Cole, Cowes |
| 2022 | Cowe | ||
| 2021 | Tom Vernon | Badger GBR 810 | Cowes |
| 2019 | Tom Vernon | Badger GBR 810 | Cowes |
| 2018 | Gavia Wilkinson Cox | Jerboa | Cowes |
| 2017 | Martin Byrne | Jaguar, IRL 201 | Cowes |
| 2015 | Cowes | ||
| 2014 | Eric Williams | Ecstatic | Cowes |
| 2013 | Klaus Diederichs | Fever | Weymouth |
| 2012 | Julia Bailey | Aimee | Cowes |
| 2011 | Andrew Craig | Chimera | Cowes |
| 2010 | Poul-Richard Hoj-Jensen | Danish Blue | Cowes |
| 2009 | Len Jones | Rumours | Falmouth |
| 2008 | Rob Campbell | Quicksilver III | Plymouth |
| 2007 | Ivan Bradbury | Elusive | Cowes |
| 2006 | L Jones | Rumours | Cowes |
| 2005 | I Bradbury | Elusive | Cowes |
| 2004 | Series Incomplete | Cowes | |
| 2003 | J Bailey | Aimee | Cowes |
| 2002 | Series Incomplete | Cowes | |
| 2001 | A Craig | Chimaera | Cowes |
| 2000 | J E Williams | Chaotic | Cowes |
| 1999 | D Sinclair | Fury | Cowes |
| 1998 | P R Hoj Jensen | Danish Blue | Cowes |
| 1997 | R Hennessy | Rascal Rat | Cowes |
| 1996 | R Hennessy | Rascal Rat | Cowes |
| 1995 | J E Williams | Hectic | Cowes |
| 1994 | M Payne | Dragon Lady | Cowes |
| 1993 | N Streeter | Sandpiper | Cowes |
| 1992 | S Fulford | Whistle | Cowes |
| 1991 | S Skakel | Bebe | Cowes |
| 1990 | J E Williams | Mayfly | Cowes |
| 1989 | Dr D Young | Jane IV | Cowes |
| 1988 | T G Wade | Avalanche | Cowes |
| 1987 | R D Brown | Sabbatical | Cowes |
