Awarded for: 1st on handicap in the club 50 mile handicap championship TT.
| Year | Winner |
|---|---|
| 1956 | J Webb |
| 1957 | R Barlow |
| 1958 | R Barlow |
| 1959 | J Webb |
| 1960 | R Cox |
| 1961 | B Austen |
| 1962 | M Jeggo |
| 1963 | R Barnett |
| 1964 | G Morris |
| 1965 | R Barnett |
| 1966 | B Austen |
| 1967 | R Barnett |
| 1968 | R Barnett |
| 1969 | - |
| 1970 | - |
| 1971 | - |
| 1972 | - |
| 1973 | M Risdale |
| 1974 | - |
| 1975 | A Rose |
| 1976 | T Rose |
| 1977 | T Rose |
| 1978 | - |
| 1979 | - |
| 1980 | - |
| 1981 | - |
| 1982 | R Richards |
| 1983 | B House |
| 1984 | M Wilson |
| 1985 | P Harris |
| 1986 | J Foster |
| 1987 | J Matthews |
| 1988 | R J Smith |
| 1989 | J Foster |
| 1990 | J Foster |
| 1991 | S Foster |
| 1992 | M Webber |
| 1993 | S Foster |
| 1994 | R Hartnell |
| 1995 | P Harris |
| 1996 | P Harris |
| 1997 | R Hartnell |
| 1998 | J Prior |
| 1999 | J Prior |
| 2000 | S Foster |
| 2001 | J Prior |
| 2002 | N Adnitt |
| 2003 | L Gardner |
| 2004 | - |
| 2005 | - |
| 2006 | - |
| 2007 | A Slack |
| 2008 | S Healey |
| 2009 | S Healey |
| 2010 | N Adnitt |
| 2011 | H Richards |
| 2012 | N Adnitt |
| 2013 | N Cooper |
| 2014 | - |
| 2015 | - |
| 2016 | N Cooper |
| 2017 | W Matthews |
| 2018 | P Harris |
| 2019 | - |
| 2020 | - |
| 2021 | - |
| 2022 | - |
| 2023 | |
| 2024 | |
| 2025 |