| Year | School |
| 2024 | Malvern Prep |
| 2023 | Malvern Prep |
| 2022 | Haverford School |
| 2021 | Malvern Prep |
| 2020 | ** None |
| 2019 | Episcopal Academy |
| 2018 | Malvern Prep |
| 2017 | Malvern Prep |
| 2016 | Germantown Academy * |
| 2016 | Malvern Prep * |
| 2015 | Haverford School |
| 2014 | Haverford School |
| 2013 | Haverford School |
| 2013 | Malvern Prep |
| 2012 | Episcopal Academy |
| 2011 | Malvern Prep |
| 2010 | Haverford School |
| 2009 | Chestnut Hill Academy * |
| 2009 | Haverford School * |
| 2009 | Malvern Prep * |
| 2008 | Malvern Prep |
| 2007 | Malvern Prep |
| 2006 | Penn Charter |
| 2005 | Malvern Prep |
| 2004 | Episcopal Academy * |
| 2004 | Germantown Academy * |
| 2004 | Penn Charter * |
| 2003 | Malvern Prep |
| 2003 | Germantown Academy * |
| 2003 | Penn Charter * |
| 2002 | Penn Charter |
| 2001 | Malvern Prep |
| 2000 | Malvern Prep |
| 1999 | Germantown Academy * |
| 1999 | Malvern Prep * |
| 1998 | Penn Charter |
| 1997 | Malvern Prep |
| 1996 | Malvern Prep * |
| 1996 | Penn Charter * |
| 1995 | Malvern Prep |
| 1994 | Malvern Prep |
| 1993 | Penn Charter |
| 1992 | Penn Charter |
| 1991 | Malvern Prep |
| 1990 | Penn Charter |
| 1989 | Malvern Prep |
| 1988 | Penn Charter |
| 1987 | Malvern Prep |
| 1986 | Malvern Prep |
| 1985 | Malvern Prep * |
| 1985 | Penn Charter * |
| 1984 | Malvern Prep |
| 1983 | Episcopal Academy * |
| 1983 | Penn Charter * |
| 1982 | Episcopal Academy |
| 1981 | Episcopal Academy |
| 1980 | Malvern Prep |
| 1979 | Malvern Prep |
| 1978 | Malvern Prep |
| 1977 | Malvern Prep |
| 1976 | Malvern Prep |
| 1975 | Malvern Prep |
| 1974 | Malvern Prep |
| 1973 | Germantown Academy |
| 1972 | Malvern Prep |
| 1971 | Haverford School |
| 1970 | Haverford School |
| 1969 | Malvern Prep * |
| 1969 | Penn Charter * |
| 1968 | Episcopal Academy * |
| 1968 | Haverford School * |
| 1967 | Penn Charter |
| 1966 | Germantown Academy |
| 1965 | Haverford School |
| 1964 | Haverford School |
| 1963 | Penn Charter |
| 1962 | Malvern Prep |
| 1962 | Penn Charter |
| 1961 | Haverford School |
| 1960 | Germantown Academy |
| 1959 | Germantown Academy * |
| 1959 | Malvern Prep * |
| 1959 | Penn Charter * |
| 1958 | Penn Charter |
| 1957 | Penn Charter |
| 1956 | Germantown Academy |
| 1955 | Penn Charter |
| 1954 | Penn Charter |
| 1953 | Episcopal Academy * |
| 1953 | Haverford School * |
| 1952 | Germantown Academy |
| 1951 | Haverford School |
| 1950 | Episcopal Academy * |
| 1950 | Germantown Academy * |
| 1949 | Episcopal Academy |
| 1948 | Episcopal Academy |
| 1947 | Episcopal Academy |
| 1946 | Episcopal Academy * |
| 1946 | Friends’ Central * |
| 1946 | Haverford School * |
| 1945 | Haverford School |
| 1944 | Haverford School |
| 1943 | Episcopal Academy |
| 1942 | Episcopal Academy |
| 1941 | Episcopal Academy |
| 1940 | Episcopal Academy * |
| 1940 | Germantown Academy * |
| 1940 | Haverford School |
| 1939 | Episcopal Academy |
| 1938 | Germantown Academy * |
| 1938 | Haverford School * |
| 1937 | Haverford School |
| 1936 | Haverford School |
| 1935 | Haverford School |
| 1934 | Episcopal Academy |
| 1933 | Germantown Academy |
| 1933 | Friends’ Central |
| 1932 | Penn Charter |
| 1931 | Haverford School |
| 1930 | Episcopal Academy |
| 1930 | Friends’ Central |
| 1930 | Penn Charter |
| 1929 | Episcopal Academy |
| 1928 | Episcopal Academy |
| 1927 | Episcopal Academy |
| 1926 | Haverford School |
| 1926 | St. Luke’s |
| 1925 | Haverford School |
| 1924 | Penn Charter |
| 1923 | Penn Charter |
| 1922 | Penn Charter |
| 1921 | Penn Charter |
| 1920 | Penn Charter |
| 1919 | Penn Charter |
| 1918 | Penn Charter |
| 1917 | Penn Charter |
| 1916 | Penn Charter |
| 1915 | Penn Charter |
| 1914 | Penn Charter |
| 1913 | Penn Charter |
| 1912 | Episcopal Academy |
| 1911 | Episcopal Academy |
| 1910 | Penn Charter |
| 1909 | Penn Charter |
| 1908 | Germantown Academy |
| 1907 | Episcopal |
| 1907 | Germantown Academy |
| 1907 | Penn Charter |
| 1906 | Penn Charter |
| 1905 | Penn Charter |
| 1904 | Haverford School |
| 1903 | Germantown Academy |
| 1902 | Haverford School |
| 1901 | Penn Charter |
| 1900 | Germantown Academy * |
| 1900 | Penn Charter * |
| 1899 | Penn Charter |
| 1898 | Germantown Academy |
| 1897 | Germantown Academy * |
| 1897 | Penn Charter * |
| 1896 | Cheltenham Military |
| 1895 | Germantown Academy |
| 1894 | Penn Charter |
| 1893 | Germantown Academy |
| 1892 | Penn Charter |
| 1891 | Haverford School |
| 1890 | Penn Charter |
| 1889 | Penn Charter |
| 1888 | Germantown Academy * |
| 1888 | Haverford School * |
| 1888 | Penn Charter * |
| 1887 | Germantown Academy |