Cayman International School is a proud member of the Caribbean Area International School Sports Association (CAISSA). This organization has a long history of facilitating international sporting events and friendship among schools in the region. Current full members of CAISSA are Carol Morgan School (the Dominican Republic), International School of Port of Spain (Trinidad & Tobago), Escuela Campo Alegre (Venezuela), Academia Cotopaxi (Ecuador), and Cayman International School.
CIS participates in three CAISSA tournaments per school year in addition to the CAISSA Middle School Sports Festival.
- Season 1: Boys and Girls Volleyball
- Boys- 4th Place, Winner of Sportsmanship Award
- Girls- 3rd Place
- Season 2: Boys Basketball and Girls Football
- Boys Basketball- DNP
- Girls Football- 2nd Place, Winner of Sportsmanship Award
- Season 3: Boys Football and Girls Basketball
- Boys Football- 4th Place
- Girls Basketball- 4th Place