Woodward had an archetypal Victorian boyhood and began to study the languages Latin, Greek, French and German by the age of eight.

[3] He received BA in 1893 and MA in 1902 and later turned to teaching and taught in several English public schools which secured him a deputy headmaster-ship.

Woodward began his teaching career at Rugby Preparatory School, where he served for a short period as an assistant master.

During his five-year period at Stamford school he spend a great deal of his time for the study of both Western and Eastern philosophy, Pali and Sanskrit, English literature, and religion.

His work at Mahinda College included taking classes in English, Latin, Pali, Buddhism and Art, in addition to the administrative duties related with the head mastership of the school.

[3] He migrated to Tasmania to live the remaining part of his life with the intention of translating the Pali Canon into English language.

In this peaceful setting he resumed his studies on Buddhism and translations for the Pali Text Society, established by Thomas Rhys Davids in 1881.

Woodward only left his home town two or three times a year, usually to take part in some activity of the local branch of the Theosophical Society.

[2][1] In 1936, after the publication of 15 volumes of a complete translation of the Digha, Majjhima, Samyutta and Anguttara Nikaya, Caroline Rhys Davids admired Woodward greatly for his untiring work for which he never expected any reward.