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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 focusses on various photographs of the pupils and staff of School House as well as various documents related to the history of the house.

This collection draws together material produced for and by the marketing department of Oakham School. Particular strengths of the collection include press cuttings and publication material (prospectuses, handbooks, maps etc.).

Press cuttings from multiple local and national newspapers have been collected together by marketing staff, gathering together news of Old Oakhamians.

Publications contain material produced for new admissions into the school and contain detailed information about uniform, curriculum, pastoral care, and general daily life of the school.

Two small red books (A and B) containing staff list, school list and school calendar for the Winter term 1980. Item A belonged to Jon Wills and item B belonged to Georgina Ridley, Form 1 pupil in Ancaster. Both items have hand-written notations and timetables are filled in.

A small red book containing staff list, school list and school calendar for the Spring term 1981; hand-written notations. Item belonged to Jon Wills.

Two small red books (A and B) containing staff list, school list and school calendar for the Winter term 1981. Item A belonged to Jon Wills and item B belonged to P.A. Rimmington. Both items have hand-written notations and amendments.

A small red book containing staff list, school list and school calendar for the Summer term 1982; hand-written notations. Item belonged to Jon Wills.

Order of service for the marriage of Kim Mortimer and Jon Wills, P.E. teachers, in the School Chapel on 23 July 1983.

A small red book containing staff list, school list and school calendar for the Spring term 1983; hand-written notations. Item belonged to Jon Wills.

Two small black books (A and B) containing staff list, school list and school calendar for the Summer term 1984. Item A belonged to Jon Wills and has hand-written notations and amendments. Those items mark the School's Quatercentenary.