The Holderness boys’ varsity basketball mantra is simple: play hard, play tough defense, and be unselfish on offense. They compete in the Lake Region League with Brewster, Kimball Union, New Hampton, Proctor, Tilton, and Vermont Academy. This is one of the most competitive leagues in the country. Holderness also competes in the NEPSAC AA class with sixteen total schools; at the end of the season the top eight teams compete in a playoff tournament. In 2015-2016, the Bulls were the #7 seed and lost to AA runner-up Cushing Academy.
Holderness basketball alumni have gone on to be successful at all levels, ranging from Division III to professional. Recent graduates have gone on to play at Stony Brook University, Dartmouth College, Siena College, Fairfield University, Norwich University, Tufts University, St. Michael's College, Endicott College, Westfield State University, and Sam Houston State University.
Woody Kampmann began coaching at Holderness in 2014. Before coming to campus, he was a college basketball coach for nine years—including seven at the Division 1 level. Most recently he coached at Boston College from 2010-14, where he helped develop two NBA draft picks (Reggie Jackson and Oliver Hanlan). Kampmann, was an assistant at Cornell from 2008-10, where he was part of three Ivy League championship teams and made three NCAA tournament appearences. The 2010 Cornell team advanced to the Sweet 16 after beating Temple and Wisconsin in the first two rounds. Kampmann is a 2005 graduate of Hobart College.