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This photographic series focuses on the history of the chapel since the laying of the foundation stone. It documents its building and opening, services held in the Chapel and objects used in everyday services.

This sub-series is related to services held in the School Chapel since the laying of the Foundation stone in 1924.

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

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

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

This series focuses on Wharflands pupils and staff since its opening in 1920. Most of the series is made of house photographs, various photographs of Housemasters and administration documents.

Oakham School Magazine, recording the Spring term 1928 (published in Summer term 1928). Contents: School Notes; O.O. Club Notes; The Chapel Fund; Fives; The Sports; Sidney Sussex Run; Boxing and Fencing Club; O.T.C.; The School Register; To G.H.; Friday Music; Lectures; Cambridge Letter; Cricket; Correspondence; Games Balance Sheet. Seven double-pages A to G.

Oakham School Magazine, recording the Spring term 1929 (published in Summer term 1929). Contents: Frontispiece; Editorial; School Notes; The Captain of the Ship; To G.H.; The Prefect's Lot; Extracts from a Wanderer's Diary; Boxing and Fencing Club; The Sports, Cricket; O.T.C.; O.O. News; Correspondence; Games Accounts. The name 'Worthington' is hand-written on the cover. Nine double-pages A to I.

Oakham School Magazine, recording the Spring term 1930 (published in Summer term 1930). It is the 46th year of the Magazine. Contents: Frontispiece; Editorial; School Notes; The Sports; A Little Egyptian; Oakham School Players; The Debating Society; O.T.C.; Cricket; O.O. News; Games Account. The name 'Worthington' is hand-written on the cover. Eight double-pages A to H.