The Weston Cup was donated by Weston Shipping who used to own the Thames Sailing Barge Gladys. This cup is awarded to the 4th barge home.
| 2021 | Repertor |
| 2020 | — |
| 2019 | Repertor |
| 2018 | Dawn |
| 2017 | Reminder |
| 2016 | Xylonite |
| 2015 | Reminder |
| 2014 | Marjorie |
| 2013 | Decima |
| 2012 | Decima |
| 2011 | Edith May |
| 2010 | Decima |
| 2009 | Repertor |
| 2008 | Reminder |
| 2007 | Adieu |
| 2006 | Gladys |
| 2005 | Mirosa |
| 2004 | Wyvenhoe |
| 2003 | Gladys |
| 2002 | Repertor |
| 2001 | Phoenician |
| 2000 | Mirosa |
| 1999 | Mirosa |
| 1998 | Portlight |
| 1997 | Portlight |
| 1996 | Portlight |
| 1995 | Portlight |
| 1994 | Wyvenhoe |
| 1993 | May |
| 1992 | Thistle |
| 1991 | Portlight |
| 1990 | Edith May |
| 1989 | Greta |
| 1988 | Repertor |
| 1987 | May |
| 1986 | Gladys |
| 1985 | May |
| 1984 | May |
| 1983 | cancelled |
| 1982 | — |
| 1981 | Repertor |
| 1980 | Mirosa |
| 1979 | Beric |
| 1978 | Mirosa |
| 1977 | Venture |
| 1976 | Gladys |
| 1975 | Northdown |
| 1974 | Redoubtable |