ATHLETICS
Playing for Cheshire sets student-athletes up for success — in college and beyond, both on and off the playing field. Our alumni have gone on to compete at some of the top universities in the nation, in the Olympics, and professionally.
70%
OF THE STUDENT BODY PARTICIPATE IN ATHLETICS
34%
OF RECENT CA GRADUATES WENT ON TO PLAY IN COLLEGE
6.6%
NATIONAL AVERAGE
20+
ATHLETIC offerings
About Cheshire Athletics
The Cheshire Academy athletics program offers 17 competitive sports programs for boys and girls, as well as a range of non-competitive athletic activities. At the Academy, students participate in a competitive team sport for two of the three seasons (fall, winter, spring) of every academic year as part of an afternoon program.
Athletics is an important priority because it encourages all students to take pride in contributing to something bigger than themselves. Students not only build new relationships with classmates, they also learn how to work as a team and support one another, they struggle and succeed together in new or higher-level challenges, and they continue to be lifelong learners through these afternoon activities.
Seasoned coaches with experience at the collegiate, semi-pro and pro levels lead many Cheshire Academy teams. In addition, coaches and assistant coaches are members of the faculty–athletes themselves–who are passionate about sports and the teams they lead.
Cheshire Academy has won more than 15 athletic championships over the last 10 years.
Cheshire Academy alumni have gone on to play at various colleges in recent years, including Brown University, Bucknell University, Colgate University, Columbia University, Dartmouth University, Fordham University, Harvard University, College of the Holy Cross, LaFayette University, University of Michigan, Princeton University, Stanford University, The University of Alabama, Worcester Polytechnic Institute, and Yale University.
At the professional level, our graduates have competed in the LPGA, NBA, NFL, and the Olympics.
Live Sports
You can find all of our livestreams in one convenient place through the hudl app on our YouTube channel! Just visit www.youtube.com/@CheshireAcademyTV/streams and make sure you are on the “live” tab. Watch basketball, football, lacrosse, soccer, or volleyball games on our page.
Athletic Schedule
| Date | Sport | Opponent | Time | Location |
|---|---|---|---|---|
| Oct 24, 2026 | Soccer - Varsity (G) |
Holy Child |
3:00PM | Away |
| Oct 24, 2026 | Volleyball - Varsity (G) |
Suffield Academy |
3:00PM | Away |
| Oct 24, 2026 | Soccer - Varsity (B) |
Wilbraham & Monson Academy |
1:00PM | Away |
| Oct 24, 2026 | X Country - Varsity (B + G) |
Hopkins School |
12:00AM | Away |
| Oct 24, 2026 | Volleyball - JV (G) |
Suffield Academy |
3:00PM | Away |
| Oct 24, 2026 | Soccer - JV (B) |
Wilbraham & Monson Academy |
1:00PM | Away |
| Oct 26, 2026 | Soccer - Varsity (G) |
Kingswood-Oxford School |
4:30PM | Home |
| Oct 28, 2026 | Soccer - Varsity (B) |
Hopkins School |
3:30PM | Away |
| Oct 28, 2026 | Soccer - Varsity (G) |
Berkshire School |
3:30PM | Home |
| Oct 28, 2026 | Volleyball - Varsity (G) |
Canterbury School |
4:00PM | Home |
| Oct 28, 2026 | Volleyball - JV (G) |
Canterbury School |
4:00PM | Home |
| Oct 28, 2026 | Soccer - JV (B) |
Hopkins School |
3:30PM | Home |
| Oct 29, 2026 | Soccer - Varsity (B) |
The MacDuffie School |
3:30PM | Away |
| Oct 30, 2026 | Soccer - Varsity (B) |
Watkinson School |
4:45PM | Home |
| Oct 30, 2026 | Volleyball - Varsity (G) |
Holy Child |
4:00PM | Home |
| Oct 30, 2026 | Football - Varsity |
Salisbury School |
6:00PM | Away |
| Oct 31, 2026 | Volleyball - JV (G) |
Holy Child |
11:00AM | Home |
| Oct 31, 2026 | X Country - Varsity (B + G) |
Williston Northampton School |
2:30PM | Away |
| Oct 31, 2026 | Soccer - Varsity (G) |
The Gunnery School |
1:30PM | Away |
| Oct 31, 2026 | Soccer - Varsity (B) |
Woodhall School |
2:30PM | Home |
| Nov 03, 2026 | Volleyball - Varsity (G) |
Kingswood-Oxford School |
5:00PM | Home |
| Nov 03, 2026 | Volleyball - JV (G) |
Kingswood-Oxford School |
5:00PM | Home |
| Nov 04, 2026 | X Country - Varsity (B + G) |
Millbrook School |
2:30PM | Away |
| Nov 04, 2026 | Volleyball - Varsity (G) |
Wilbraham & Monson Academy |
3:00PM | Away |
| Nov 04, 2026 | Soccer - Varsity (G) | 2:30PM | Away | |
| Nov 04, 2026 | Soccer - Varsity (B) |
Kingswood-Oxford School |
2:30PM | Away |
| Nov 04, 2026 | Soccer - JV (B) |
Kingswood-Oxford School |
2:30PM | Away |
| Nov 05, 2026 | Volleyball - Thirds |
Wooster School |
4:30PM | Away |
| Nov 06, 2026 | Soccer - Varsity (B) |
The Forman School |
6:00PM | Home |
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Updates

Cheshire Academy’s Dr. Alex Conaway Published in TEACH Magazine
The lessons of athletics reach far beyond the scoreboard. Dr. Alex Conaway, associate dean of students for school culture and belonging, explains in TEACH Magazine

Cheshire Academy Associate Dean Shares Power of Athletics in Southington Magazine
Dr. Alex Conaway discusses how team sports provide an authentic building ground for resilience, perspective, other key life skills Dr. Alex Conaway, Cheshire Academy’s associate dean of students for

10 New Faculty Join Cheshire Academy for 2026-27
Each brings a wealth of experience and talent to academics and student support services Cheshire Academy welcomed 10 new faculty members for the 2026-27 academic year, including classroom teachers and