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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.

A prospectus promoting studying at Oakham School in 1951. Contents: School History; Trustees and Staff; Curriculum; Boarding Houses; Clothes and Uniform; Health; Sports, Activities and Societies; Fees; Scholarships; Day Boys. Seven double-pages A to E. Enclosed is a list of staff (F).

A prospectus promoting studying at Oakham School in 1946. Contents: Foundation & History; The School today; Situation & Surroundings; Trustees; Premises & Equipment; School Terms, Holidays, Timetable; Chapel Services, Religious Instruction; Curriculum; Libraries; Reports; Boarding Houses; School House, Wharflands, Deanscroft, The Junior House, Hodge Wing; Clothes; Diet & Tuck Boxes; Health; Absence & Leave; Games; Physical Education; J.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. Seven double-pages A to G. Enclosed are two trustees and staff lists (H and I) in 1946 and 1949.

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

A registrar's report for the year 1987. Contents: Examinations; Public Relations; Statistics and the Computer; Numbers in School; Third form Boarding girl entry. Attached are numbers for the academic year 1986-1987 (annexe A), numbers in the School by houses (annexe B), comparison of registrations 1983-1987, numbers in the School boy-girl ratio (annexe C). Nine pages A to I.

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).

A yellow notebook recording the performance of candidates who took the entrance examination in 1977.

A red notebook with lists of names for Junior Entry, including the waiting list and the registration, from January 1959 to 1989.

This series relates to various annual reports presented to the Trustees, including Headmaster's reports, Registrar's reports and Second Master's reports. The series spans over three Headmasters, John Buchanan, Richard Bull and Graham Smallbone.