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This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

An account book recording pupils' fees, staff wages, various income and expenditure from Summer term 1930 to Easter term 1939.

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

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

Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

This series focusses on the headmastership of Francis Cecil Doherty (1929-1935) 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 F.C. Doherty.

A School list for the Summer term 1932 organised from Form VI to Form I, for School House, Wharflands, Greylands, Junior House, Miss Daniell's House and the Day Boys.

This file focusses on admission prospectuses and various publications in the 1930s.