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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 calendar of events in the Spring term 1949. Hand-written note on the cover reads 'Best wishes, JM'. Three double-pages A to C.

An edition of Matkin's almanack including a section on Oakham School on page 16.

A detailed itinerary for the visit of Prince Philip to Oakham School on 8 November 1957. Three pages A to C.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

This sub-series focuses on photographs of boys in School House since the 1940s.

A photograph of the boys in School House in the academic year 1952-1953 under the Housemaster John Moore.

A photograph of the boys in School House in the academic year 1951-1952 under the Housemaster John Moore.

A photograph of the boys in School House in the academic year 1950-1951 under the Housemaster John Moore, with signatures at the back. Attached are two photocopies of the photograph, with attempts to names the boys. Five pages A to E.

A photograph of the boys in School House in the academic year 1954-1955 under the Housemaster John Moore.