Harold attended school at Mill Hill and during his spare time helped his father produce the first edition of the OED. By the time Harold had finished school and was preparing to leave for university, he had been responsible for over 27,000 quotation that later appeared in the OED.
He had won a place at Balliol College, Oxford and in 1890 he graduated with a first degree in Mathematics and became an assistant master at Queen's College, Tauton and later at Carlisle Grammar School. In 1896 he became headmaster of Ormskirk Grammar School in Lancashire.
On January 4, 1897 he married Miss Kate Maitland Crosthwaite.
In 1901 he was appointed a school inspector and in 1928 he became a member of the board of education.
In 1897 he was encouraged by Baron von der Lasa (who had just completed his book on the history of European chess) to research into the further past of chess. In order to do this he learnt Arabic (in addition to his native English, and German) and examined many historical chess documents, in 1913 his research resulted in his most significant work a History of Chess, a work which today is still used as a standard reference, supporting the theory that chess originated from India.
Other works include:
