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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 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.

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 letter from C.C. Love to John Barber regarding "The Story of Oakham School" and "Operation Oakham", and sharing some memories of his time at school.

This series focuses on the life of the Day boys of Ruddles in the 1970s.

This sub-series focuses on photographs of Day Boys of Ruddles House in the 1970s.

A photograph of the Day Boys of Ruddles House in 1972 under the Housemaster R.M. Davies.

A photograph of the Day Boys of Ruddles House under the Housemaster R.M. Davies.

Notes on the organisation and administration of the Junior School, written by Patrick Wilson, Master-in-charge of Jerwoods. Includes information on house staff, daily routine, weekend activities and contact with parents.

This series focuses on the Junior Day boys' house of Sargants, since 1959. The main items are house photographs, photographs of the prefects and handbooks.