This was presented by David and Emma Gowing of Sailorman Films Ltd, the cup is named after his film ‘Sailorman’ and is awarded to the 2nd barge home.
| 2021 | Blue Mermaid |
| 2020 | Ironsides |
| 2019 | Edme |
| 2018 | Niagara |
| 2017 | Niagara |
| 2016 | Niagara |
| 2015 | Niagara |
| 2014 | Edith May |
| 2013 | Niagara |
| 2012 | Cambria |
| 2011 | Decima |
| 2010 | Repertor |
| 2009 | Melissa |
| 2008 | Decima |
| 2007 | Marjorie |
| 2006 | Marjorie |
| 2005 | Xylonite |
| 2004 | Phoenician |
| 2003 | Edme |
| 2002 | Xylonite |
| 2001 | Marjorie |
| 2000 | Marjorie |
| 1999 | Marjorie |
| 1998 | Marjorie |
| 1997 | Marjorie |
| 1996 | Mirosa |
| 1995 | Mirosa |
| 1994 | Repertor |
| 1993 | Edme |
| 1992 | Edme |
| 1991 | May |
| 1990 | Reminder |
| 1989 | Repertor |
| 1988 | Mirosa |
| 1987 | Mirosa |
| 1986 | Mirosa |
| 1985 | Xylonite |
| 1984 | Reminder |
| 1983 | cancelled |
| 1982 | — |
| 1981 | Marjorie |
| 1980 | May |
| 1979 | Mirosa & Xylonite |
| 1978 | May |
| 1977 | May |
| 1976 | Lady Daphne |
| 1975 | May |
| 1974 | May |
| 1973 | Venture |
| 1972 | Kitty |