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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.

A School list of staff and pupils for the Summer term 1903. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1902; Oxford & Cambridge Board, 1903; Royal Drawing Society. Five double-pages A to E.

A list of Trustees, Old Oakhamians, Parents of present boys and Personal friends who raised the Sargant Presentation Fund in order that an organ might be placed in Oakham School Memorial Chapel. The book was presented to Walter Lee Sargant by Colonel Sir Herbert Bryan on 26 July 1930 when the organ was dedicated. Thirteen pages A to M.

A book compiling the minutes of the Trustees' Financial Committee meetings.

An edition of Matkin's almanack including a section on Oakham School on page 16.

This series relates to the Finance Committee of the Trustees, in particular minutes of their meetings.

A compilation of hand-written notes, organised chronologically into Headmasters. It is thought that they were used as research material on the history of Greylands. Pages A to F.

A School list of staff and pupils for the Summer term 1915. Contents: Trustees; Teachers; Forms VI to I; Honours List; List of Exhibitions and Prizes gained during the year; Royal Drawing Society.

This collection focuses on the administrative side of the school including admissions and trustees.

There is a rich collection of admissions books dating back to the 19th century alongside detailed notes of Trustees' committee minutes and development plans.

School inspections undertaken by external bodies are represented in this sub-fond and include some of the 19th century schemes which helped to found the school as one independent from Uppingham.

ADM/4 contains policy documents outlining the health and safety measures in the school.