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This series focuses on the Junior House/Chapmans pupils and staff since its opening in 1910. It first comprised the Junior Department with facilities for boys boarders and classrooms. The house was renamed Chapmans in September 1960, after Frank Emerson Chapman, first Housemaster of the Junior House; it became a Senior House. Most of the series is made of photographs, house photographs as well as more informal photographs.

Three school reports (A to C) for Henrietta Lea in her first year at Oakham School.

Order of service of the service of thanksgiving for Bob Duesbury held at the School Chapel. A letter from Dr Robert Stevens to Jon Wills is attached and enclosing a copy of his Address. Six pages A to F.

This file relates to Michael Stevens, Acting Headmaster for two terms in 1985. The bulk of the collection is letter to Parents.

A letter from the Acting Headmaster Michael Stevens to Parents regarding the term's sports achievements, Music concerts, Drama news and the influenza vaccination.

A small red book containing staff list, school list and school calendar for the Winter term 1965; hand-written notations and amendments. Item belonged to Michael Stevens.

A small red book containing staff list, school list and school calendar for the Winter term 1977; hand-written notations. Item belonged to Michael Stevens. It is the first Red Book of Richard Bull's headmastership.

Two small red books (A and B) containing staff list, school list and school calendar for the Summer term 1980. Item A belonged to Michael Stevens and item B belonged to Mrs 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 Spring term 1985; hand-written notations. Item belonged to Mrs P.A. Rimmington. It is the first Red Book under Michael Stevens as Acting Headmaster.

A complete collection of bound books, gathering Old Oakhamian Magazines copies, from 1899 to 2002. Some books may contain issues of the Magazine that would be otherwise missing in the collection.