The Second Boys' Squash team practices every day at the same time that the First Boys' team practices and as a single team. This makes for intense practices during which the Second team players are pushed to develop their squash skills and to become ever more competitive by the more experienced and talented First team players. This also means that Second Boys' Squash players get instruction from both the First and Second team coaches on a daily basis. Traveling together, the two teams also compete against the same schools at the same time. 

The Westminster squash program emphasizes sportsmanship above all else, but historically it has also been a very successful program at both the First and Second team levels. Over the past ten years, Second Boys’ Squash has compiled a match record of 84-46-2 against the very best New England prep schools. Many of the younger Second team players go on to compete for the First Team before they graduate.