- Bulger Lowe
- Nils V. "Swede" Nelson
- Man of the Year
- Walter Brown
- Joseph P. Zabilski
- Joe Concannon
- John Baronian
- Joseph P. McKenney
- Head Coach of the Year
- Asst Coach of the Year
- Henry Smith Courage
- Dr. Joseph H. Burnett
- William J. Stewart Jr.
- William H. Ohrenberger
William J. Stewart Jr. Award
To the high school football official of the year. Named in honor of William J. Stewart Jr., long time coach of three sports at Boston English High School and a legendary official at the professional, college, and high school levels.
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| Erle Garrett 2019 |
Jack Walsh 2019 |
William E. Lannon III 2013 |
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| Jay Gledhill 2012 |
William Reinertson, Sr. 2011 |
Angelo Scaccia 2010 |
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| Jim Kearney 2009 |
William J. Stewart III 2008 |
Paul Sheehan 2007 |
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| Eugene Ferris 2006 |
Ronald Boudreau 2005 |
Bill O'Brien 2004 |
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| Dave McCarthy 2003 |
Bill Barrett 2002 |
Thatcher Carl 2001 |
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| Ken Eldridge 2000 |
Prior to 2000:
Bill McDonald
Patrick Santin
Bill Leaneus
Bill McDonald
Peter Brady
Paul Lyons
Paul Howard
Al Sheehan
Tom English
Bill Lanagan
George Murphy
Bob Donovan