

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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| 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