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A letter from Edward Simpson congratulating John Barber on the publication of "The Story of Oakham School" and sharing his memories of the school during the Second World War.

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.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

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.

A prospectus promoting studying at Oakham School in 1943. 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; 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. Six double-pages A to F. Enclosed is a list of Trustees and Staff (G).

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).