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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 sub-series relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.

This file focusses on correspondence regarding the refurbishment of Old School in the late 1980s-early 1990s and the issue concerning the frescoes.

A letter from the Headmaster Graham Smallbone to Lt Col the Lord Charteris of Amisfield regarding the history of Old School, and the restorations carried out by architects.

A letter from the Headmaster Graham Smallbone to O.O. Henry Blagg regarding the press coverage of the debate concerning the frescoes in Old School and the plan for the restoration of the building.

A letter from the Headmaster Graham Smallbone to Dr Elizabeth Cumming regarding preserving the frescoes in Old School whilst trying to restore the historical building, and discussing the press coverage of the debate.

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.

An account of Oakham School with illustrations written by the Headmaster, Walter Lee Sargant in the early 20th century. Contents: Preface; Foundation and Old School; Curriculum and Examinations; Boarders and Houses; Notes on School Life; The Junior House.