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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.

This file focusses on roll call lists from the early 20th century, under the headmastership of Walter Lee Sargant.

This file focusses on various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.

Old Oakhamian Calendar, published in 1907. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1907; Old Oakhamian Notes; Old Boys' Matches; O.O. Club Accounts. A note on the inside cover from John Barber regarding the years of publication of this magazine. Six double-pages A to F.

This focusses on photographs of the Headmaster, Walter Lee Sargant, as well as various photographs of Oakham town in the early 20th century.

Old Oakhamian Calendar, published in 1910. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1910; Old Oakhamian Notes; Old Boys' Matches; O.O. Club Accounts. Seven double-pages A to G.

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.

Old Oakhamian Calendar, published in 1913. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1913; Old Oakhamian Notes; Old Boys' Matches; O.O. Club Accounts.

Old Oakhamian Calendar, published in 1921. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1920; Letter from the Headmaster with plan; Old Oakhamian Notes; Old Boys' Matches. Six double-pages A to F.

Old Oakhamian Calendar, published in 1924. Cover with contents: Editorial; List of Addresses of Members of the Old Oakhamian Club - 1924; Meeting of Old Oakhamian Club; Old Oakhamian Luncheon; A Letter from the Headmaster; Cambridge Letter; Officers' Training Corps; A Weekend in Africa; Births, Deaths and Marriages; Old Oakhamian Matches; School Staff - September 1924. Nine double-pages A to I.