Past Massachusetts Teachers of the Year
  | 2007 | Jessie Auger, Boston |
| 2006 | Suzanne Wintle, Bolton |
| 2005 | Nancy Tyler Schoen, Franklin |
| 2004 | Melinda A. Pellerin-Duck, Reading |
| | 2003 | Jeffrey R. Ryan, Reading |
| 2002 | Dawn Eileen McNair, Newton |
| 2001 | Marianne V. Moran, Methuen |
| | 2000 | David F. Lussier, Andover |
| 1999 | Bruce M. Penniman, Amherst |
| 1998 | Mary C. Ginley, Longmeadow |
| 1997 | Leonard Swanton, Lexington |
| 1996 | Kathleen Sherman, Falmouth |
| | 1995 | Jerry Howland, Boston |
| | 1994 | Virginia Freyermuth, Duxbury |
| | 1993 | Steven Levy, Lexington |
| | 1992 | Ronald Adams, Quincy |
| | 1991 | Charles Sposato, Framingham |
| | 1990 | Molly Murphy, Brookline |
| | 1989 | Marjorie Montgomery, Newton |
| | 1988 | James McDermott, Worcester |
| | 1987 | Margot Desjardins, Westport |
| | 1986 | Donna Viveiros, Fall River |
| | 1985 | Francis Smith, Wayland |
| | 1984 | Cathleen Hughes, Scituate |
| | 1983 | Donald Pottle, Shrewsbury |
| | 1982 | Joseph Kelly, Lexington |
| | 1981 | Margaret Campbell, Longmeadow |
| | 1980 | Marta Valdes, Boston |
| | 1979 | Rita Croteau, Worcester |
| | 1978 | Olive Craigwell, Boston |
| | 1977 | Martin Badoian, Canton |
| | 1976 | Barbara Boschert, Worcester |
| | 1975 | no selection |
| | 1974 | Thais Waldron, Reading |
| | 1973 | Marcia Hayes, Boston |
| | 1972 | Marcia Fowler, Ipswich |
| | 1971 | Robert Anastas, Framingham |
| | 1970 | Lucille Thimblin, Tantasqua Reg. |
| | 1969 | Ruth Doorly, Westwood |
| | 1968 | Neil Fitzgerald, New Bedford |
| | 1967 | John Moulton, Brookline |
| | 1966 | Leah Benway, Southwick |
| | 1965 | Vivian Little, Hampden-Wilbraham |
| | 1964 | Edna Penwarden, Arlington |
| | 1963 | no selection |
| | 1962 | Lottie Perry, Norton |
| | 1961 | no selection |
| | 1960 | Edward Frude, Shelburne Falls |
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