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

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 1942. 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 is modifications to the clothes list due to Rationing in July 1941 (J).

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.

The Old Oakhamian Magazine, published in 1954. Contents: Editorial; Annual General Meeting; Annual Dinner; Regional Meetings; War Memorial Fund; O.O. Fund; Barraclough Hall; School News; O.O. Notes; Life in Kenya; Presidents of the Club; Engagements, Births, Marriages & Deaths; Obituaries; New Members; Changes of Address; Jobs for the (Old) Boys; Notices; Correspondence; Golf. Ten double-pages A to J.

A bound copy of several Old Oakhamian Magazines from 1953 to 1959.

Individual salary and wages sheets for teaching and support staff between 1937 to 1960. Pages A to BB.

This sub-series contains various items related to Junior House/Chapmans. The bulk of the sub-series is informal photographs of everyday life in the boarding house in the 1950s/1960s.

Two bound copies of several Oakhamian Magazines from 1960 to 1963. Item A has a black cover; item B has a brown cover.

A salaries cash book, recording salary, payments, tax, and lunch for teaching staff, admin staff and matrons, from May 1963 to November 1965.