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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 various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.

Extract from a 1940 prospectus, published in the Old Oakhamian Magazine. Content: Size; Staff; Fees; Curriculum; Timetable; Diet & Tuck boxes; Games; Activities outside the classroom; Day Boys. Three pages A to C.

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 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.

This file focusses on letters sent by Headmaster Richard Bull during his headmastership (1978-1984). The bulk of the collection is made of letters sent to Parents.

A letter from the Headmaster Richard Bull to Parents regarding influenza vaccination, Leave-Outs and Exeats for overseas pupils, the use of Oakham Sports facilities by parents, and future term dates.

The Ancaster house diary for the years 1983 to 1989 with notes on the everyday life of the house, absences, house events, school information about the girls (Pastoral), letters to/from parents and house sports teams.

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

The Ancaster house diary for the years 1989 to 1998 with notes on the everyday life of the house, absences, house events, school information about the girls (Pastoral), letters to/from parents, house sports teams and results, programmes of house and school events.