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This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

Round House development revised proposals report, prepared by Pick Everard Architects, including an introduction; the proposals on the new layouts, plans; estimated Costs of the project; drawings and photographs.

A sepia toned, oval framed photos of All Saints Church. The photograph was taken by John Burton & Sons, and the date is estimated between 1863 and 1911.

Issue of the "Rutland Record. Number Three. 1982/1983" which includes an article by John Barber entitled 'Oakham School 140 years ago', p. 118 - 121.

A letter from G.R. Compton, Acting Senior Traffic Management Officer at the Leicestershire Constubulary, to Jan West regarding safety measures during the Rutland Water Walk.

Four letters, collated on one A3 sheet, addressed to the Headmaster Tony Little and Charles Welch, to thank them for various events such as the Harvest Party in 1997 and Oakham School's contribution to the Andrew Martin Trust.

A menu for the anniversary dinner to commemorate the centenary o the Battle of Hohenzollern Redoubt held at the 4/5th Battalion, The Royal Leicestershire Regiment Officers' Dining Club on 10 October 2015. The item includes a photograph of the officers of the 1/4th Leicestershire Regiment at Luton in October 1914 and their signatures, the menu and the provenance of twelve candlesticks.

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).

This sub-series contains books used by pupils during services in chapel or books published by staff or Old Oakhamians and given to the school. A large part of this sub-series contains hymns books compiled by Rev T.C.H. Clare ('29).

A compilation of addresses spoken in the School Chapel, collated by G. Talbot Griffith, Headmaster, and dedicated to Neddy Cowell on 20 May 1956. This book was published and sold for the benefit of the Oakham School War Memorial Fund.