Henry R. Woodrooffe was educated at Brighton College and at Christ Church College, Oxford, where he was awarded the degree Master of Arts (MA). He married Elizabeth M. Oak, with whom he had five children. From 1856 to 1864 he served as a missionary in the Eastern Cape. He then returned to England and was curate of Ryton, county Durham, from 1865 to 1867. Returning to the Cape Colony he was appointed colonial chaplain on 1 December 1868 and served as rector of Somerset East to 1885. In 1879 the University of the Cape of Good Hope admitted him to the MA degree on the basis of his degree from Oxford University. In February 1883 he was appointed acting deputy inspector of schools, initially in the Transkei, and after receiving a fixed appointment in November 1885 continued as deputy inspector of schools until 1897. From the eighteen-seventies to 1911 he served as a canon of the (Anglican) Church of the Province of South Africa in Grahamstown, and from 1909 to 1911 as archdeacon of Cradock. He was a co-translator of the Book of common prayer into Xhosa and was a member of the Board of Revisers of the Xhosa Bible.
In 1898 Woodrooffe presented a very rare plant, Broomeia congregata (a so-called puff-ball, or globular fungus) to the Government Herbarium. At that time only six specimens of this plant were known to the governemt botanist, P. MacOwan*. In 1910 he met the anthropologist H. Balfour* in Grahamstown. Woodrooffe had himself collected archaeological material at Somerset East, and this same year he presented it to the Pitt Rivers Museum, Oxford.