Winsor has a rich tradition in athletic competition. Our athletes and coaches strive for excellence in each of our fourteen different sports. These are the teams that represent Winsor's goal of athletic achievement through teamwork.

Basketball

E.I.L. Champions
1993–94
1994–95
1997–98
2003–04
2006–07


Crew

Head of the Charles Youth Fours Champions
1992
2002
2003
2004

Head of the Charles Youth Eight Champions
1993
1994
 
Henley Champions
2003
 
N.E.I.R.A. Champion Fours
2002
2010
2016

N.E.I.R.A. Team Trophy
2008
2010
2011
2013
2014
2015

2016
2017
 
NEIRA Youth Four Champions
2016

U.S.R.A. Youth Four Champions
2000
2002
2003


Cross Country

E.I.L. Champions
2001
2002
2003
2004
2005
2006
2007
2008
2009
2010
2012
2015
2016
2017
2018
2019
2021

New England Division I Runner Up
2019

New England Division II Champions
2013


Field Hockey

E.I.L. Champions
1990
1995
1996

New England Class C Finalist

2012

NEPSAC Class C Champions
2018
2021


Ice Hockey

E.I.L. Champions
2003-04
2004-05

Lacrosse

E.I.L. Champions
1991
1993
1994
1995
1996
1997
1998
1999
2000
2001

2002

Sailing

Mass Bay League Champions
1992

Softball

E.I.L. Champions
1995
1997
2013
2019

Soccer

E.I.L. Champions
1990
1993
1994
1995
2002
2004
2006
2010
2011

Squash

E.I.L. Champions
2009–10
2010–11
2011–12
2012–13
2013–14
2014–15
2015–16
2016–17
2017–18
2018–19
2019–20
2021–22

New England Class A third place
2021–22

US High School Division 3 Champions
2011

New England Class B Champions
2011–12

Swim Team

E.I.L. Champions
2007–08
2008–09
2018–2019

Tennis

E.I.L. Champions
1991
1992
1994
1995
1996
2006
2019
2022


New England Class B Champions
2022

New England Class C Semi-Finalist
2013
2019

New England Class C Finalist
2014
 

Track

E.I.L. Champions
2015
2016
2017
2018
2019
2022