The Hollis Brookline wrestling team was established in 1989 under it's first head coach, Rhon Rupp. Rupp coached the Cavaliers to 2-New England Champions, several Meet of Champion and IMS/Division II Champions, as well as the programs 1st Division II Team Championship in 2007 over his 20-year career. Hollis Brookline is also home to the 1st National All-American in New Hampshire History, Dusty Rich (1996). With his stepping down after the 2008-09 season, Rupp turned the program over to former Cavalier wrestler, and New England Champion, Brian Bumpus. HB has since won two Division II championships (2012, 2013), and crowned 10 DII and 1 MOC champion, as well as only the 3rd New England finalist in HB history, Casey Quinn (2012).