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This series focusses on the headmastership of Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

A prospectus promoting studying at Oakham School in 1897. Contents: Trustees & Staff; Subjects; Upper School & Lower School; Examinations; Boarding Houses; Library, Games & Extras; Terms; Holidays; Infectious Disease; Scholarships, Exhibitions & Prizes. Three double-pages A to C.

A prospectus promoting studying at Oakham School c.1909, with illustrations. Contents: Trustees & Staff; Brief History of the School; Subjects of Instruction; Upper School & Lower School; Boarding Houses; Health; Games; Holidays; Term's fees Scholarships and Exhibitions.

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

A comment from John Buchanan to The Jerwood Foundation, London on Oakham School Academic Report 1980-1981, discussing scholars, Oxbridge, and school fees. Eleven pages A to K.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

A letter from the Headmaster Richard Bull and the Chairman of Trustees T.C.S. Haywood to Parents regarding the building of a new Biology Block, including plans, and the pre-payment of fees scheme III. Two pages A and B.

This file relates to Michael Stevens, Acting Headmaster for two terms in 1985. The bulk of the collection is letter to Parents.

A prospectus promoting studying at Oakham School in 1956. Contents: Introduction; School Terms & holidays; Timetable; Chapel services; Curriculum; Reports; Boarding Houses; Diet; Health; Absence & Leaves; Games; C.C.F.; Scouts and Cubs; Clothes; Entry; Fees; Pocket Money; Notice of Leaving; Scholarships; Leaving Scholarships; Expenses; Appointments with Headmaster; Day Boys; Old Oakhamian Club. Six double-pages A to F.

A prospectus promoting studying at Oakham School in 1937. Contents: Trustees & Staff; Foundation & History; The School today; Situation & Surroundings; Premises & Equipment; School Terms, Holidays, Timetable; Chapel Services, Religious Instruction; Curriculum; Libraries; Reports; Boarding Houses; School House, Wharflands, The Junior House; Clothes; Diet & Tuck Boxes; Health; Absence & Leave; Games; Physical Education; O.T.C.; Scouts; Activities outside the classroom; Entry, Fees, Remission of Fees for absence; Optional Payments, Extras; Pocket Money; Scholarships; Leaving Scholarships; Notice of leaving; Expenses; Appointments with the Headmaster; Day Boys; Publications; Old Oakhamian Club. Nine double-pages A to I. Enclosed are a form of application for admission (J) and a clothes list for the Junior House (K).