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A prospectus promoting studying at Oakham School in 1922. Contents: Trustees & Staff; Brief History of the School; Subjects of Instructions; Boarding Houses; Buildings; Scale of Fees; Health; Scholarships and Exhibitions.

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 bound copy of several Oakhamian Magazines from 1911 to 1919.

Oakham School Magazine, recording the Winter term 1910 (published in Spring term 1911). Contents: School Notes; Officers' Training Corps; A Son of Empire; Mr. A.C. Johnson, Late Hereditary Trustee; The Concert; Rome; Wild Nature's Way; Caravan and Camera; Football; Correspondence. Seven double-pages A to G.

A bound copy of several Oakhamian Magazines from 1935 to 1937.

A book compiling the minutes of the Trustees' Financial Committee meetings.

A letter from O.O. Lt Col Jim Fife to the Headmaster Graham Smallbone regarding the frescoes in Old School.

A brief history of School House written by Jim O'Kane. Four double-pages A to D.

This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

A letter from Margaret Kamester to Ms Hoare, Headmaster's Secretary, regarding information about the Old School frescoes and enclosing an entry for Mary Florence-Sargant.