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| 1900-1902 | Mrs. Franz E. Zerrahn | The Country Club |
| 1902-1907 | Miss Grace B. Keyes | Concord C.C. |
| 1907-1913 | Miss Louisa A. Wells | The Country Club |
| 1913-1914 | Mrs. E.C. Wheeler Jr. | Wollaston G.C. |
| 1915-1916 | Miss Harriot I. Curtis | The Country Club |
| 1917-1920 | Miss Eleanor W. Allen | Oakley C.C. |
| 1921-1922 | Mrs. Donald M. Belcher | Winchester C.C. |
| 1923-1924 | Mrs. Raynor M. Gardiner | Weston G.C. |
| 1925-1929 | Miss Fannie C. Osgood | Brae Burn C.C. |
| 1930-1933 | Miss Eleanor W. Allen | Oakley C.C. |
| 1934-1937 | Miss Frances E. Stebbins | Brae Burn C.C. |
| 1938-1941 | Miss Margaret Curtis | The Country Club |
| 1942-1943 | Miss Deborah Verry | Tatnuck C.C. |
| 1944-1945 | Miss Frances E. Stebbins | Brae Burn C.C. |
| 1946-1947 | Mrs. Edward H. Baker | Oakley C.C. |
| 1948-1949 | Mrs. Henry B. Jackson | The Country Club |
| 1950-1951 | Mrs. Henri F. Prunaret | Charles River C.C. |
| 1952-1953 | Mrs. Donald M. Belcher | Winchester C.C. |
| 1954 | Miss Frances E. Stebbins | Brae Burn C.C. |
| 1954-1957 | Mrs, Charles F. Eaton, Jr. | Duxbury Yacht Club |
| 1958-1959 | Mrs. Winthrop G. Dow | Dedham C&P Club |
| 1960-1963 | Mrs. Edward L. Peirson | Salem C.C. |
| 1964-1965 | Mrs. Vincent Farnsworth, Jr. | Winchester C.C. |
| 1966-1967 | Mrs. Paul L. Hutchinson | Brae Burn C.C. |
| 1968-1971 | Mrs. Paul G. Black | Marshfield C.C. |
| 1972-1975 | Mrs. Howard H. Grayson | Pine Brook C.C. |
| 1976-1977 | Mrs. J. Paul Sheeran | Winchester C.C. |
| 1978-1979 | Mrs. Samuel E. Cutler, Jr. | Concord C.C. |
| 1980-1981 | Mrs. E. Norman Peterson, Jr. | Duxbury Yacht Club |
| 1982-1983 | Mrs. William Scheft | Belmont C.C. |
| 1984-1985 | Mrs. John J. Sullivan | Wollaston G.C. |
| 1986-1987 | Mrs. David D. Parker | Wellesley C.C. |
| 1988-1989 | Mrs. Hatheway E. White | Westborough C.C. |
| 1990-1991 | Mrs. Gregory Savian | Ipswich C.C. |
| 1992-1993 | Miss H. Louise Mariani | Braintree G.C. |
| 1994-1995 | Mrs. James F. Tobin | Bellevue G.C. |
| 1996-1997 | Mrs. Robert L. Fish | Concord C.C. |
| 1998-1999 | Suzanne E. Nelson | Charles River C.C. |
| 2000-2001 | Sara Hastings Foehl | Dedham C&P Club |
| 2002-2003 | Susan J. Dean | Foxborough C.C. |
| 2004-2005 | Judith A. Norton | Indian Ridge C.C. |
| | 2006-2007 | Pamela S. Green | Belmont C.C. |
| | 2008-2009 | Anne Farrington | The Country Club |
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