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This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

A history titled 'Oakham Through the Centuries', written by former Headmaster W.L. Sargant. Contents: from prior to the Saxon occupation to the end of the 18th century. Hand-written note on the cover reading 'With best wishes for the new year, W.L.S.' Five double-pages A to E.

This file focusses on publications, histories and articles, written by Walter Lee Sargant during his headmastership and his retirement. The items relate to the history of Oakham School and Oakham town.