Brewster has captured 7 National Prep Championships since 2010. Also, the program has won 7 NEPSAC Class AAA Tournament Championships since 2008. Over the past 15 seasons, the program has averaged over 30 victories per year and has a winning percentage of 87%. Brewster has captured 10 regular-season NEPSAC Class AAA Championships since 2008. The program has advanced to the National Final Four 11 times since 2008.

20 Brewster alumni have played in the NBA, while 50+ others have had professional careers in leagues around the world, including the NBA G League. 11 alumni have been selected in the NBA Draft since 2010.

Since 2001, the program has sent over 170 players to Division I schools, including: Stanford University, Georgetown University, University of North Carolina, University of Kansas, University of Michigan, Syracuse University, University of Kentucky, University of Virginia, University of California-Los Angeles, Vanderbilt University, Brown University, Princeton University, Cornell University, Harvard University, and Columbia University.

The basketball program is increasingly attracting the attention of colleges and universities across the country. This past year representatives from more than 100 schools have visited campus to watch our student-athletes.

The goal of Brewster's boys' prep basketball program is to play competitively within the NEPSAC Class AAA division and to be in a position to qualify for postseason play in the New England Tournament, as well as the National Prep Championships. While striving for a successful competitive record, coaches also teach team play, provide players with the best coaching in fundamental offensive and defensive skills, and help players grow in self-confidence and self-esteem.