Henfry made his senior debut for Perth during the 1937 season, aged 16 years and 49 days, with only seven other players known to have debuted at a younger age. He played twice at state level during the 1939 season, at the age of 17, and then finished second to Haydn Bunton in the 1941 Sandover Medal. During the Second World War, Henfry served in the Australian Defence Force, initially as a private in the Australian Army, and then as a flight lieutenant in the Royal Australian Air Force. While training in Sydney, he played for a RAAF team in the New South Wales Australian National Football League, which included several VFL and SANFL players, including captain Alby Morrison. In 1944, while based in Victoria, he played two games for Carlton. When the war ended, he remained in Victoria, and Carlton requested a clearance from Perth to enable him to play for them. He was forced to sit out the 1946 season as Perth did not agree to a clearance, but was then able to captain Carlton for the 1947 season. It was a successful year, with Carlton defeating Essendon in a one-point thriller in the Grand Final. The season was capped off when he shared Carlton's best and fairest award with his close friendBert Deacon, who also won the Brownlow Medal that year, Carlton's first. Henfry placed fourth in the Brownlow count. In 1949, after some controversy, he captained Victoria against Western Australia, being only the second man to represent Victoria after first representing Western Australia. Returning to Western Australia before the 1953 season, Henfry captain-coached Perth for two seasons before retiring from playing. He remained as non-playing coach, and in 1955 coached Perth to its first premiership since 1907, with the club winning the grand final by two points over. Henfry remained Perth's coach until the 1959 season, and then again from the 1962 season through to the 1964 season, overall coaching the club in 242 games with a win rate of 57.4%. He also coached the state team in six matches during the 1956 and 1957 seasons, including at the 1956 Australian National Football Carnival, held in Perth, with WA placing second. During the 1961 season, during the gap between his years coaching Perth, Henfry coached the University of Western Australia's side in the Western Australian Amateur Football League to an A-grade premiership. Henfry died in Inglewood, a suburb of Perth, in January 2007, aged 85. He had been an inaugural inductee into the West Australian Football Hall of Fame in 2004, and was posthumously inducted into the Australian Football Hall of Fame in 2014.
