Boys' Tennis Tournament Champions:
1988 - The Phelps School
1989 - Woodlynde School
1990 - Woodlynde School
1991 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
1992 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
1993 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
1994 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
1995 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
1996 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
1997 - ?
1998 - The Phelps School
1999 - The Phelps School
2000 - ?
2001 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2002 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2003 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2004 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2005 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2006 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2007 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2008 - Jack M. Barrack Hebrew Academy
2009 - Jack M. Barrack Hebrew Academy
2010 - Jack M. Barrack Hebrew Academy
2011 - Jack M. Barrack Hebrew Academy
2012 - Jack M. Barrack Hebrew Academy
2013 - Jack M. Barrack Hebrew Academy
1989 - Woodlynde School
1990 - Woodlynde School
1991 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
1992 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
1993 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
1994 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
1995 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
1996 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
1997 - ?
1998 - The Phelps School
1999 - The Phelps School
2000 - ?
2001 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2002 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2003 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2004 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2005 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2006 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2007 - Akiba Hebrew Academy (currently Jack M. Barrack Hebrew Academy)
2008 - Jack M. Barrack Hebrew Academy
2009 - Jack M. Barrack Hebrew Academy
2010 - Jack M. Barrack Hebrew Academy
2011 - Jack M. Barrack Hebrew Academy
2012 - Jack M. Barrack Hebrew Academy
2013 - Jack M. Barrack Hebrew Academy