2006 Middlesex Varsity LAX
2006 Middlesex Varsity Field Hockey
2007 Middlesex Varsity LAX
2006 MX Varsity Field Hockey vs Lawrence - Qtr Final
2007 Middlesex Varsity Field Hockey
2007 Middlesex Varsity Field Hockey vs St. Georges
2007 Middlesex Varsity Field Hockey - ISL Quarter Finals vs Cushing
5/1/2008 - Middlesex vs St. Georges
10/13/2012 - Varsity Football - Nobles vs Thayer
5/1/2008 - Middlesex vs. St. Marks
51/2008 - Middlesex vs. St. Pauls
5/1/2008 - Middlesex vs. Tabor
5/7/2008 - Middlesex vs. Governors
2008 Middlesex Prom
5/12/2008 - Middlesex vs BBN
2007 Middlesex Varsity Field Hockey - ISL Semi-Finals vs. St. Marks
2008 - Middlesex Varsity Field Hockey vs Lawrence
10/22/2011 - Girls Varsity Soccer - Middlesex vs Nobles
5/18/2013 - Boys Varsity Baseball - Middlesex vs Belmont Hill
5/18/2013 - Boys Varsity Lacrosse - Middlesex vs Belmont Hill
5/20/2015 - Boys Varsity Lacrosse - Governor's Academy vs Middlesex
11/02/2016 - Boys Varsity Soccer - Middlesex vs Nobles
11/4/2016 - Varsity Field Hockey - Middlesex vs Exeter
12/2/2016 - Boys Varsity Hockey - Dexter vs Middlesex
1/13/2018 - Girls Varsity Hockey - Middlesex vs Governor's Academy
11/14/2018 - Boys Varsity Soccer - NEPSAC Class B Quarterfinal - Groton vs Middlesex
12/15/2018 - Harrington Invitational - Middlesex vs Nobles
2/6/2019 - Boys Varsity Hockey - Middlesex vs Roxbury Latin
9/25/2019 - Varsity Field Hockey - Tabor vs Middlesex
10/30/2019 - Boys Varsity Soccer - Nobles vs Middlesex
12/11/2019 - Boys Varsity Hockey - Brooks vs Middlesex
10/13/2021 - Girls Varsity Soccer - Middlesex vs Governor's Academy
10/13/2021 - Varsity Field Hockey - Middlesex vs Governor's Academy
11/3/2021 - Boys Varsity Soccer - Nobles vs Middlesex
12/10/2021 - Boys Varsity Hockey - Middlesex vs Berwick
4/13/2022 - Boys Varsity Lacrosse - St. Sebastian's vs Middlesex