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A letter from the Headmaster Tony Little to Parents reviewing events of Spring term 2000. Contents: School rules; Music, Drama; Debating; Physics Olympiad; Sports achievements; Future dates.

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.

A book recording dates and times of services in the School Chapel, including the initials of the officiant, the attendance, the preacher, and the collections from Winter term 1991 to Spring term 2014.

This sub-file contains various photographs of Derek Grant, English teacher.

This sub-series contains various items related to Junior House/Chapmans. The bulk of the sub-series is informal photographs of everyday life in the boarding house in the 1950s/1960s.