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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 compilation of addresses spoken in the School Chapel, collated by G. Talbot Griffith, Headmaster, and dedicated to Neddy Cowell on 20 May 1956. This book was published and sold for the benefit of the Oakham School War Memorial Fund.