Despite the long trail of becoming a National Champion in order to achieve the entry list, then winning the event itself, several competitors have achieved the honour more than once.
Phil Crebbin, Richard Estaugh and Laurie Smith have each won the event twice, whilst Jim Hunt has achieved that honour three times.
By 2008 three competitors, Ian Southworth, Geoff Carveth and Nick Craig had held the trophy four times, whilst the record holder, Mike Holmes, achieved the Championship honours five times over a span of eighteen years from 1978 to 1995. The return of Carveth in 2009 added an extra element of suspense - would Carveth or Craig achieve five wins to equal the achievement of Holmes? In the event Carveth, on top form, ably crewed by Emma Clarke, was the clear winner, nine points clear in the final results to equal the five wins of Holmes. 2010, the Fiftieth Anniversary of the Endeavour Championship could see that record broken...
| 2009 | G Carveth | Emma Clarke | RS200 |
| 2008 | N Craig | T Lewis | B14 |
| 2007 | S Tylecoat | T Lewis | Firefly |
| 2006 | N Craig | J Stewart | RS400 |
| 2005 | N Craig | J Stewart | Finn |
| 2004 | N Craig | K Bedborough | OK |
| 2003 | R Gilbert | J Stewart | RS400 |
| 2002 | G Carveth | C Davies | RS800 |
| 2001 | J Hunt | P Hobson | Solo |
| 2000 | J Hunt | P Hobson | Solo |
| 1999 | G Carveth | C Davies | RS200 |
| 1998 | R Estaugh | S Potts | GP 14 |
| 1997 | J Hunt | T Freer | National Enterprise |
| 1996 | I Renilson | S Roberson | Contender |
| 1995 | M Holmes | G O'Brien | RS400 |
| 1994 | C Howarth | R Estaugh | GP 14 |
| 1993 | G Carveth | P Rowley | Solo |
| 1992 | G Carveth | P Rowley | Solo |
| 1991 | J Lee | S Thompson | International Cadet |
| 1990 | M Holmes | ? | National Albacore |
| 1989 | I Pinnell | A Service | National Enterprise |
| 1988 | I Southworth | D Hayes | GP 14 |
| 1987 | N Marsden | K Cribben | National Enterprise |
| 1986 | A Gillard | C Machin | National Enterprise |
| 1985 | I Southworth | R Drumgold | International 420 |
| 1984 | I Southworth | D Hayes | Lark |
| 1983 | I Southworth | D Hayes | GP 14 |
| 1982 | M Holmes | M Cochran | National Albacore |
| 1981 | R Estaugh | N Thompson | GP 14 |
| 1980 | M Holmes | M McNamara | GP 14 |
| 1979 | L Smith | P Barker | International Fireball |
| 1978 | M Holmes | D Froggatt | National Albacore |
| 1977 | L Smith | P Barker | International Fireball |
| 1976 | E Owen | S Stewart | GP 14 |
| 1975 | P Crebbin | A Landamore | International 470 |
| 1974 | P Crebbin | A Landamore | National Albacore |
| 1973 | N Martin | Caroline Lougher | National Firefly |
| 1972 | P Milanes | P Nash | Flying Dutchman |
| 1971 | F Williams | R Sheffer | Merlin Rocket |
| 1970 | R Suggitt | Mandy Watchman | Heron |
| 1969 | M Rimmer | R Suggitt | National Enterprise |
| 1968 | R Hennessy | R Michael | National Enterprise |
| 1967 | W Bacon | M McNamara | National Enterprise |
| 1966 | B Ellis | K Ellis | Merlin Rocket |
| 1965 | M McNamara | M Rimmer | National Albacore |
| 1964 | R Pitcher | R Amos | Flying Dutchman |
| 1963 | D Newman | R Martin | National Firefly |
| 1962 | M Evans | R Smith | National 12 |
| 1961 | P Bateman | K Musto | International Cadet |








