| SENIOR ROAD RACE CHAMPIONSHIP (The Leo/Caspian Cup from 2011) (Previously The Stapleford Tawney Trophy) |
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| Year | Name | ||
| 1948 | BARNET C.C. | ||
| 1949 | GLENDENE C.C. | ||
| 1950 | ILFORD R.C. | ||
| 1951 | SUFFOLK ROADS C.C. | ||
| 1952 | KENTISH WHEELERS | ||
| 1953 | COMET C.C. | ||
| 1954 | NORWOOD PARAGON C.C. | ||
| 1955 | Not Awarded | ||
| 1956 | WHITEWEBBS C.C. | ||
| 1957 | MARSH R.C. | ||
| 1958 | BALHAM C.C. | ||
| 1959 | HAINAULT R.C. | ||
| 1960 | CATFORD C.C. | ||
| 1961 | CATFORD C.C. | ||
| 1962 | CAMBRIDGE TOWN AND COUNTY | ||
| 1963 | WELWYN WHEELERS | ||
| Year | Name | Club | |
| 1964 | BRIAN LAPWORTH | ||
| 1965 | BERNARD DEAMER | ||
| 1966 | JOHN GREATWOOD | ||
| 1967 | JOHN GREATWOOD | ||
| 1968 | C. KUBICKI | ||
| 1969 - 1971 | Not Awarded | ||
| 1972 | SID LOVATT | Finsbury Park C.C. | |
| 1973 | JOHN CLAREY | Gemini B.C. | |
| 1974 - 1975 | Not Awarded | ||
| 1976 | G. JENNINGS | ||
| 1977 | ROBERT CRAYFORD | Gravesend C.C. | |
| 1978 | J. HOLMES | Gravesend C.C. | |
| 1979 | DAVID ROBERTS | Hainault R.C. | |
| 1980 | CRAIG STEVENS | Becontree Wheelers C.C. | |
| 1981 | CRAIG STEVENS | Becontree Wheelers C.C. | |
| 1982 | PETER BONFIELD | Welwyn Wheelers | |
| 1983 | GEOFFREY SAXON | VS De Merck | |
| 1984 | COLIN LANDER | Southend & County Wheelers | |
| 1985 | TREVOR NUTTER | Bishop's Stortford C.C. | |
| 1986 | JIM ATTRILL | Becontree Wheelers C.C. | |
| 1987 | MIKE BUTTIGIEG | Southend & County Wheelers | |
| 1988 | COLIN LANDER | Southend & County Wheelers | |
| 1989 | STEVEN SHAKESPEARE | Leo R.C. | |
| 1990 | MATTHEW ILLINGWORTH | Olympia Sport | |
| 1991 | ANTHONY WALLIS | Olympia Sport | |
| 1992 | RICHARD HARE | Southend & County Wheelers | |
| 1993 | STUART SHAND | Olympia Sport | |
| 1994 | PETER BONFIELD | Welwyn Wheelers | |
| 1995 | GARY BAKER | Olympia Sport | |
| 1996 | GARY BAKER | Olympia Sport | |
| 1997 | MATTHEW MILES | West Kent R.C. | |
| 1998 | GARY BAKER | Angliasport | |
| Race stopped due to RTA - Gary Baker leading at that time | |||
| 1999 | GARY BAKER | Angliasport | |
| 2000 | CHRIS BROOKING | Cambridge C.C. | |
| 2001 | GARY BAKER | Angliasport | |
| 2002 | DUNCAN ALEXANDER | Apibikes.com | |
| 2003 | MICHAEL MERRALLS | Apibikes.com | |
| 2004 | GARY BAKER | Angliasport | |
| 2005 | NATHAN MILLER | Angliasport | |
| 2006 | KEVIN CHAMBERS | API | |
| 2007 | BEN THOMPSON | Glendene C.C. | |
| 2008 | DANIEL PATTEN | PCA Ciclos Uno | |
| 2009 | NEIL CHAPMAN | Maldon & District C.C. | |
| 2010 | JONATHAN SHUBERT | Verulam C.C. | |
| 2011 | OWEN LAKE | Cambridge C.C. | |
| 2012 | JAMES ROSS | C.C. Ashwell | |
| 2013 | LLOYD CHAPMAN | Glendene C.C. | |
| 2014 | WILLIAM DRURY | Glendene C.C. | |
| 2015 | GRAY TURNOCK | Finsbury Park C.C. | |
| 2016 | MIKE WRAGG | C.C. Luton | |
| 2017 | VOJTECH BLAZEJOVSKY | PMR @ Toachim House | |
| 2018 | LOUIS BILYARD | Lee Valley Youth C.C. | |
| 2019 | SAMUEL ASKER | Lee Valley Youth C.C. | |
| 2020 - 2022 | Event Not Held | ||
| 2023 | COLIN WARD | Essex Roads C.C. | |
| 2024 | OSKAR EVERETT | Lee Valley Youth C.C. | |
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