Typically at Middlesex, younger athletes can hope to rise quickly to varsity teams, and seniors are almost always part of the team experience. Out of these experiences, community building is a natural for everyone. Underclassmen are required to play three seasons each year. Though Upperclassmen's requirements are progressively more lenient, most students still participate beyond the requirement. Athletics at Middlesex provide a valuable social medium in which students can form relationships with their faculty coaches, as well as with each other.
Many athletes go on to play sports for the most competitive colleges in the country.