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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 sub-file is made of various bills on Augustus Padley's account in the first half of 19th century.

A school bill for the half-year ending at Christmas 1837 on A.F. Padley's account; detailing fees for tuition, laundry, books, subjects, uniform and allowance.

A programme for an amateur performance given by the students to celebrate the opening of the new buildings of Oakham Grammar School on 8 September 1858.

This series focusses on the headmastership of Rev Robert Tabraham (1875-1878) and of Rev Henry Walter Fitch (Acting Headmaster, 1878) and contains items relating to the life at School in the second half of the 19th century.

This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

A School list of staff and pupils for the Summer term 1902. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1901; Oxford & Cambridge Board, 1902; Royal Drawing Society. Five double-pages A to E.

A roll call for School House, Mr. Scriven's, Mr Williams', Bank House and the Day Boys in Winter term 1887. One name has been hand-written in Form VI.

Photocopies of two pages (A and B) from The Oakham School Magazine, Winter term 1888, pages 3-4.

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.