H.H. Stephenson was born at Esher, Surrey, on 3 May 1833, the son of a surgeon — an unusual social background for a Victorian professional cricketer. He turned professional in his teens and made his first-class debut for Surrey against Kent at the Oval in 1853. By 1856 he was a regular in F.P. Miller's championship side; by 1857 he had made the All-England Eleven. Stephenson bowled right-arm fast roundarm with a high action, batted in the middle order, and not infrequently kept wicket — a useful versatility on tour. He was selected for Parr's North America tour in September 1859 and was one of the leading bowlers there; the same combination of skills would lead Spiers and Pond, the Melbourne caterers, to choose him over Parr to captain the first Australian tour in 1861-62. His peak as a batsman came later, in 1864 and 1865, when he scored 824 and 788 runs and made all three of his first-class hundreds. He retired after his benefit in 1871 and went on to coach at Uppingham School until his death.