The Independent School Athletic Conference (ISAC) is the interscholastic league in which the Middle School (Grades 5-8) Osprey teams play. Participation is held in high regard as is learning fair play and sportsmanship. We offer soccer, volleyball, and basketball within that league. Additional athletic opportunities are available in tennis, distance running, and fitness.
Many student-athletes play for Osprey teams enjoying the camaraderie of their peers at Chesapeake. Some also participate in additional high level competition in swimming, soccer, basketball, baseball, and softball available in the surrounding region.
Improvement and playing to our potential are more important than winning. Winning is sometimes the result of the ability to play under pressure, which is emphasized on the Varsity teams. Respect for the ability of each team member, home team and opponent, is essential to our success in athletics. We aspire to “win without boasting and lose without excuse.” 
Many of the ISAC’s athletes play together on teams in leading independent high schools, and so supporting excellent teamwork and personal improvement prepares them for future endeavors.
Chesapeake Academy has a Field Day in the Spring for students in Grades K-8.