| 2022-2023 | Andrew Linkenhoker, Smith Vocational |
| 2021-2022 | Ernest Houle, Assabet Valley |
| 2020-2021 | Jon Evans, Keefe Tech. |
| 2019-2020 | Stephen Dockray, Tri-County Regional |
| 2018-2019 | John Lafleche, Bay Path Regional |
| 2017-2018 | James Quaglia, Blue Hills |
| 2016-2017 | Robert Dutch, Upper Cape Tech. |
| 2015-2016 | John Lavoie, Greater Lawrence |
| 2014-2015 | Thomas Hickey, South Shore Regional |
| 2013-2014 | Edward Bouquillon, Minuteman |
| 2012-2013 | Luis Lopes, Southeastern |
| 2011-2012 | Roger Bourgeois, Essex Aggie |
| 2010-2011 | Barbara Renzoni, Tri-County Regional |
| 2009-2010 | David Papagni, Bay Path Regional |
| 2008-2009 | Richard Gross, Bristol Plymouth |
| 2007-2008 | Amelia O’Malley, North Shore Tech. |
| 2006-2007 | Frank Llamas, Smith Vocational |
| 2005-2006 | Barry Motta, Upper Cape Cod Regional |
| 2004-2005 | John Kosko, South Shore Regional |
| 2003-2004 | James Hager, Southeastern |
| 2002-2003 | James Santos, Bristol County |
| 2001-2002 | Eugene Carlo, Assabet Valley |
| 2000-2001 | James Brosnan, Northern Berkshire |
| 1999-2000 | David Ferreira, Old Colony |
| 1998-1999 | Richard Morse, Norfolk Agricultural |
| 1997-1998 | John Jones, Tri-County Regional |
| 1996-1997 | Charles Lyons, Shawsheen |
| 1995-1996 | Stratos Dukakis, Montachusett |
| 1994-1995 | Wilfrid Savoie, Blue Hills |
| 1993-1994 | Pat Carlson, North Shore Tech. |
| 1992-1993 | Paul Bento, Keefe Tech. |
| 1991-1992 | Gene Pickard, Blackstone |
| 1990-1991 | Dave Filkins, Franklin Tech. |
| 1989-1990 | Lou Gleason, Greater Lawrence |
| 1988-1989 | David Sampson, Upper Cape Code Regional |
| 1987-1988 | Jeff Riley, Greater New Bedford |
| 1986-1987 | Paul O’Leary, Southeastern |
| 1985-1986 | Ken Custy, Tri-County Regional |
| 1984-1985 | Janet Doe, Worcester |
| 1983-1984 | Mike Fitzpatrick, Pathfinder |
| 1982-1983 | Joe Mazzaralla, Quincy |
| 1981-1982 | Bob Butler, Worcester |
| 1980-1981 | Jim O’Neil, Franklin County |
| 1979-1980 | Dave Tobin, Assabet Valley |
| 1978-1979 | Jerry Paist, Pathfinder |
| 1977-1978 | Jim Gibbons, Pittsfield |
| 1976-1977 | Bernholdt Nystrom, Nashoba Tech. |
| 1975-1976 | Mary Ellen Cronin, New Bedford |
| 1974-1975 | John Dwyer, Worcester |
| 1973-1974 | Dan Donahue, Keefe Tech. |
| 1972-1973 | Fred Teed, South Shore Regional |
| 1971-1972 | Walter Janiak, New Bedford |
| 1970-1971 | Paul Sullivan, Blackstone |
| 1969-1970 | John Collins, Weymouth |
| 1967-1968 | Bill Dwyer, Blue Hills |
| 1966-1967 | Bill Dwyer, Blue Hills |
| 1965-1966 | Don Graves, Planning Board |
| 1965-1966 | Bill Dwyer, Planning Board |
| 1965-1966 | Paul Sullivan, Planning Board |
| 1965-1966 | Fred Teed, Planning Board |