- Housatonic Valley Athletic League (HVAL): Christian Heritage, Chase Collegiate, Forman, Master's (CT), South Kent, Harvey, Watkinson and Wooster comprise the HVAL. The varsity sports played in the HVAL include cross country, boys soccer, girls soccer, girls volleyball, boys basketball, girls basketball, baseball, softball, boys tennis, girls tennis, boys lacrosse, golf, and ultimate frisbee.
- New England Prep School Athletic Conference (NEPSAC): Wooster is in the Western division (District IV) of this league - called the Western New England Prep School Athletic Association (WNEPSAA). There are individual coaches associations for every sport we participate in (i.e. Western New England Prep School Women's Basketball Association, Western New England Prep School Women's Lacrosse Association, etc.)