The Arthur Bowles Cup was presented by Nancy and Tom Gray in memory of Nancy’s father, Arthur Bowles, who was a Brightlingsea man who worked and raced on the water and is awarded to the 2nd smack home.
| 2021 | Kate CK52 |
| 2020 | Kate CK52 |
| 2019 | Maria CK21 |
| 2018 | Alberta CK318 |
| 2017 | My Alice CK348 |
| 2016 | Maria CK21 |
| 2015 | Alberta CK318 |
| 2014 | Alberta CK318 |
| 2013 | My Alice CK348 |
| 2012 | Fly MN17 |
| 2011 | Maria CK21 |
| 2010 | Maria CK21 |
| 2009 | Ethel Alice CK476 |
| 2008 | Maria CK21 |
| 2007 | Maria CK21 |
| 2006 | Pioneer CK18 |
| 2005 | Primrose CK273 |
| 2004 | Ellen CK222 |
| 2003 | Kate CK52 |
| 2002 | Sunbeam CK328 |
| 2001 | Lizzie Annie MN23 |
| 2000 | Lizzie Annie MN23 |
| 1999 | Sunbeam CK328 |
| 1998 | Martha II MN69 |
| 1997 | Sunbeam CK328 |
| 1996 | Charlotte Ellen CK258 |
| 1995 | Lizzie Annie MN23 |
| 1994 | Charlotte Ellen CK258 |
| 1993 | Sunbeam CK328 |
| 1992 | Laura FD319 |
| 1991 | Charlotte Ellen CK258 |
| 1990 | Laura FD319 |
| 1989 | Charlotte Ellen CK258 |
| 1988 | Charlotte Ellen CK258 |
| 1987 | Charlotte Ellen CK258 |
| 1986 | ADC CK431 |
| 1985 | Charlotte Ellen CK258 |
| 1984 | Hyacinth CK256 |
| 1983 | cancelled |
| 1982 | — |
| 1981 | Ethel Alice CK476 |
| 1980 | Gracie CK46 |
| 1979 | Hyacinth CK256 |
| 1978 | Hyacinth CK256 |
| 1977 | Hyacinth CK256 |
| 1976 | — |
| 1975 | G&A CK76 |
| 1974 | Peace CK171 |
| 1973 | Peace CK171 |
| 1972 | ADC CK431 |
| 1971 | Hyacinth CK256 |