Principals of Medfield High School
* Medfield High School Officially Established on March 24, 1870
| 1870 | Henry F. Kurt | |
| 1870-1871 | Mr. Marvel | |
| 1871-1872 | Walter S. Parker | |
| 1872-1873 | William L. Whittemore | |
| 1873-1874 | Cornelius E. Wood | |
| 1874-1875 | Miss Wardwell | |
| 1875-1878 | William E. Marshall | |
| 1878-1879 | Walter H. Small | |
| 1879-1882 | Charles N. Bently | |
| 1882-1883 | Clarence E. Griffin | |
| 1883-1884 | Miss E.J. Towle | |
| 1884-1889 | E. Emmons Grover | |
| 1889-1890 | Eugene F. DeNormandie | |
| 1890-1892 | Edwin H. Whitehill | |
| 1892 | George C. Burrage | |
| 1892-1895 | Charles Guild | |
| 1895-1897 | Daniel G. Munson | |
| 1897-1900 | Walter Van Kleek | |
| 1900-1901 | Leonard M. Patton | |
| 1901-1903 | Clarence H. Jones | |
| 1903-1904 | * Medfield High School closed, students sent toDedham and Walpole High Schools | |
| 1904-1907 | Thomas H. Kenworthy | |
| 1907-1909 | William J. Chisholm | |
| 1909-1912 | Norval B. Spinney | |
| 1912-1918 | Ralph W. Taylor | |
| 1918-1919 | C. Harold Risley | |
| 1919-1947 | Alton H. Hartford | |
| 1947-1949 | Raymond S. Locke (Headmaster) | |
| 1949-1952 | Charles E. Benton | |
| 1952-1955 | William H. McLin | |
| 1955-1970 | Charles F. Mains | |
| 1970-1974 | Russell H. Johnson | |
| 1974-1991 | Tassos P. Filledes | |
| 1991-1999 | Robert C. Maguire | |
| 1999-2000 | Judith E. Noble (Interim Principal) | |
| 2000-2003 | Ann Ashworth | |
| 2003-2007 | Andrew Keough | |
| 2007-2011 | Judith E. Noble | |
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