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| Year | Name | School Committee |
| 2021 | Ellen Holmes | Ashburnham-Westminster Reg. |
| 2020 | Deborah Davis | Northeast Metropolitan Voc. Tech. |
| 2019 | Devin Sheehan | Holyoke |
| 2018 | Beverly Hugo | Northeast Metropolitan Voc. Tech. |
| 2017 | Patrick Murphy | Barnstable |
| 2016 | Jacob Oliveira | Ludlow |
| 2015 | Patrick Francomano | King Philip Regional |
| 2014 | Ann Marie Cugno | Medford |
| 2013 | Mary Jo Rossetti | Somerville |
| 2012 | Penny Blackwell | Upper Cape Cod Voc. Tech. |
| 2011 | Dorothy Presser | Lynnfield |
| 2010 | Kathleen Robey | Marlborough |
| 2009 | Debra (Bibeau) LaValley | Amesbury |
| 2008 | Ellen Furtado | Swansea |
| 2007 | Joseph Santos | Ludlow |
| 2006 | Maurice Hancock | Brockton |
| 2005 | Kenneth Pereira | Upper Cape Cod Reg. Voc. Tech |
| 2004 | Paul Schlichtman | Arlington |
| 2003 | Carol LePrevost | Lee |
| 2002 | Rosemary Sandlin | Agawam |
| 2001 | Robert Gass | Randolph |
| 2000 | Nancy Stinger | East Longmeadow |
| 1999 | Lynn Ryan | Assabet Valley Voc-Tech |
| 1998 | Brian O'Connell | Worcester |
| 1997 | Scott McDuffy | Brockton |
| 1996 | Albert Roderick | Falmouth |
| 1995 | Janice Mills | Mashpee |
| 1994 | Carl Petersen | Salem |
| 1992-93 | Winthrop Farwell | Brockton |
| 1991-92 | Lynne Sullivan | Newton |
| 1990-91 | Francis Elliot | Quaboag Regional |
| 1989-90 | Carol Grazio | Groveland/Pentucket Reg. |
| 1988-89 | Norman Doyle | Newburyport |
| 1987-88 | Christopher Kennedy | Quincy |
| 1986-87 | Roberta Doering | Agawam |
| 1985-86 | John Coleman | Beverly |
| 1984-85 | Frank Hegarty | Avon |
| 1983-84 | William Carey Jr. | Arlington |
| 1982-83 | Mary Whitney | Fitchburg |
| 981-82 | Doris Krensky | Plymouth-Carver Reg. |
| 1980-81 | Charlotte Scott | Nashoba Valley Voc. Tech |
| 1979-80 | John Raftery | Hull |
| 1978-79 | Robert Jacobsen | Williamstown |
| 1977-78 | Joseph Savory | Lee |
| 1976-77 | Gertrude Florini | Beverly |
| 1975-76 | John Silva | Hull |
| 1974-75 | Paul Amber | Natick |
| 1973-74 | Margaret Jacques | Grafton |
| 1972-73 | John Canavan Jr | Winthrop |
| 1971-72 | Hugh Boyd | Stoneham |
| 1970-71 | Robert Miller | Danvers |
| 1968-70 | Helen Bowditch | Worcester |
| 1966-68 | Edward Butler | Duxbury |
| 1964-66 | Charles Sweeney | Quincy |
| 1962-64 | Alton Cavicchi | Plymouth |
| 1961-62 | Philip Weissbrod | Lenox |
| 1959-61 | Shirley Lewis | Taunton |
| 1958-59 | John McDonough | Springfield |
| 1957-58 | Haskell Freedman | Newton |
| 1956-57 | Charles Johnson | Tyringham |
| 1955-56 | Theodore Sargent | Swampscott |
| 1954-55 | Hazel Johnson | Stoneham |
| 1953-54 | Honore Savaria | West Springfield |
| 1952-53 | Thomas Moriarty | Fitchburg |
| 1951-52 | Elmer Poole | Dartmouth |
| 1950-51 | George Harper Jr. | Williamstown |
| 1949-50 | Charlotte Roads | Marblehead |
| 1948-49 | Winston Keck | Shrewsbury |
| 1947-48 | Ethel Troland | Malden |