Boys cross country was started at Punahou as a club sport in 1956 to help develop distance runners for the track program through a longer training season. It was incorporated into the list of ILH activities in 1958 and the HHSAA in 1965.
The Punahou girls cross country program was started in 1972, with an initial turnout of six runners. Undefeated in the first season, Punahou won the first girls cross country ILH championship trophy. With two leagues organized, the first girls HHSAA meet was held in 1973 at Pali Golf Course. Punahou won the first individual title and the first state championship trophy.
The success the Punahou cross country squads have enjoyed is attributed to team depth. In the 1965 Inaugural State Championships, a team of unchallenged potential surged to a first place finish. In later years Punahou runners would achieve unprecedented individual successes in state competitions, capturing first and second place in consecutive seasons.
The growth of cross country can be traced through the Punahou Invitational Run, which draws runners from all islands. In 1956, 18 runners from three high schools participated, and at its 40th anniversary in 1995 more than 200 runners from 27 schools toed the starting line.