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Stephen B Leslie Sportsmanship Award

2019- Michael McAllister (SailMaine)
2018- Chris Lukens (The Hotchkiss School)

2014-2017 - Not Awarded
2013 - Mary Farrel (BC High)
2012 - Bob Gaftney (Sharon HS), Warren Hathaway (Dartmouth HS), Griff Fenton (Mount Desert Isle HS), Leo Constantino (Moses Brown School)
2011 - Portsmouth Abbey
2010 - Marblehead HS
2009 - Duxbury HS
2008 - Not Awarded
2007 - George Stevens Academy
2006 - Martha's Vineyard RHS
2005 - Not Awarded
2004 - Not Awarded
2003 - Not Awarded
2002 - Henry Maxwell (the Williams School)
2001 - Not Awarded
2000 - Not Awarded
1999 - Christopher Patterson & Patrick Rynne (St. Sebastian's School)
1998 - Jordon Smith (Hingham HS) & Falmouth HS Sailing Team
1997 - Diana Weidenbacker (Boston University Academy)
1996 - Ted Conrads & Jeff Condon (Brunswick School)
1995 - Tabor Academy Sailing Team