Challenge Cup Winners - PSA Head of the River
| Year | School |
|---|---|
| 1905 | Guildford |
| 1906 | Scotch |
| 1907 | Scotch |
| 1908 | Scotch |
| 1909 | CBC |
| 1910 | CBC |
| 1911 | CBC |
| 1912 | CBC |
| 1913 | Scotch |
| 1914 | THS |
| 1915 | CBC |
| 1916 | CBC |
| 1917 | CBC |
| 1918 | THS |
| 1919 | THS |
| 1920 | Scotch |
| 1921 | CBC |
| 1922 | THS |
| 1923 | CBC |
| 1924 | Guildford |
| 1925 | THS |
| 1926 | CBC |
| 1927 | CBC |
| 1928 | CBC |
| 1929 | CBC |
| 1930 | CBC |
| 1931 | CBC |
| 1932 | Scotch |
| 1933 | Hale |
| 1934 | Scotch |
| 1935 | Scotch |
| 1936 | Scotch |
| 1937 | Scotch |
| 1938 | Scotch |
| 1939 | Hale |
| 1940 | Scotch |
| 1941 | Scotch |
| 1942 | Aquinas (unofficial) |
| 1943 | Aquinas |
| 1944 | Hale |
| 1945 | Hale |
| 1946 | Aquinas |
| 1947 | Hale |
| 1948 | Guildford |
| 1949 | Aquinas |
| 1950 | Aquinas |
| 1951 | Hale |
| 1952 | Hale |
| 1953 | Hale |
| 1954 | Hale |
| 1955 | Hale |
| 1956 | Hale |
| 1957 | Scotch |
| 1958 | Christ Church |
| 1959 | Christ Church |
| 1960 | Scotch |
| 1961 | Christ Church |
| 1962 | Guildford |
| 1963 | Christ Church |
| 1964 | Christ Church |
| 1965 | Aquinas |
| 1966 | Aquinas |
| 1967 | Scotch & Christ Church |
| 1968 | Scotch |
| 1969 | Aquinas |
| 1970 | Aquinas |
| 1971 | Hale |
| 1972 | Aquinas |
| 1973 | Aquinas |
| 1974 | Aquinas |
| 1975 | Aquinas |
| 1976 | Aquinas |
| 1977 | Aquinas |
| 1978 | Scotch |
| 1979 | Christ Church |
| 1980 | Aquinas |
| 1981 | Christ Church |
| 1982 | Aquinas |
| 1983 | Hale |
| 1984 | Scotch |
| 1985 | Scotch |
| 1986 | Christ Church |
| 1987 | Aquinas |
| 1988 | Guildford |
| 1989 | Aquinas |
| 1990 | Scotch |
| 1991 | Hale |
| 1992 | Christ Church |
| 1993 | Guildford |
| 1994 | Aquinas |
| 1995 | Aquinas |
| 1996 | Trinity |
| 1997 | Aquinas |
| 1998 | Aquinas |
| 1999 | Trinity |
| 2000 | Hale |
| 2001 | Wesley |
| 2002 | Christ Church |
| 2003 | Christ Church |
| 2004 | Trinity |
| 2005 | Christ Church |
| 2006 | Christ Church |
| 2007 | Trinity |
| 2008 | Christ Church |
| 2009 | Trinity |
| 2010 | Trinity |
| 2011 | Christ Church |
| 2012 | Christ Church |
| 2013 | Trinity |
| 2014 | Christ Church |
| 2015 | Scotch |
| 2016 | Trinity |
| 2017 | Guildford |
| 2018 | Hale |
| 2019 | Christ Church |
| 2020 | No race conducted |