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1988-1989 Lionel Bishop Old Town High School
1989-1990 George M. Davis, Jr. Winslow High School
1990-1991 Robert Clement Madison Area Memorial High School
1991-1992 J. David Shapiro Deering High School
1992-1993 Robert E. Liebow Mount Desert Island High School
1993-1994 Ansel Stevens, Jr. Bonny Eagle High School
1994-1995 Jeff Sturgis Leavitt Area High School
1995-1996 James Pouravelis Bonny Eagle Middle School
1996-1997 Roger Lachapelle Lewiston High School
1997-1998 Steven Galway Edward Little High School
1998-1999 Raymond Bussiere Bangor High School
1999-2000 Allan Young Sanford High School
2000-2001 Marc Gousse Edward Little High School
2002-2003 John Pinkerton Lincoln Academy
2003-2004 Jennifer Vitiello Westbrook High School
2004-2005 Lynn M. Brown Bonny Eagle High School
2005-2006 Nancy Nicolson Sanford High School
2007 Mary Nadeau Nokomis Regional High School
2008 Christopher Record Oxford Hills Comprehensive  High School
2009 Anthony Bourbon Marshwood Middle School
2010 Julie Smyth Loranger Middle School
2011 Lori Napolitano Bonny Eagle High School
2012 Laurie Wood South Portland High School
2013 Michael Lane Sacopee Valley Middle School
2014 Kelli Deveaux Windham High School
2015 (NAESP) Kimberly O’Donnell Buxton Center Elementary School
2015 (NASSP) Joshua Ottow Yarmouth High School
2016 (NAESP) Joshua Levy Harriet Beecher Stowe Elementary School
2016 (NASSP) Paula Callan Messalonskee High School
2017 (NAESP) Ann Hanna Ocean Avenue School
2017 (NASSP) Melanie Smith Messalonskee Middle School
2018 (NASSP) Jayme Jones Greely High School
2019 (NASSP) Kimberlee Bennett South Portland High School
2020 (NAESP) Tricia Campbell Boothbay Region High School
2020 (NASSP) Erin Maguire Bonny Eagle High School
2021 (NAESP) Jessica Dyer Ridge View Community School
2021 (NASSP) Megan Hayes Teague Mt. Ararat Middle School
2022 (NASSP) Phillip Rossetti Windham High School
2023 (NASSP) Lowell Oyster Bonny Eagle Middle School
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