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This sub-series focuses on photographs of boys, living in Junior House/Chapmans since its inception. The bulk of the collection gathers photographs from the 1950s to 1980s.

A photograph of the boys in Junior House in 1911 under the Housemaster Frank Chapman.

A photograph of the boys in Junior House in 1913 under the Housemaster Frank Chapman. The name 'Fritham House' is written on the back.

This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

The Oakhamian Magazine, recording the Summer term 1941 (published in Winter term 1941). Contents: Roll of Honour; School News; Frank Emerson Chapman; Music Notes; J.T.C.; A.T.C.; Scout Notes; Swimming Sports; Football; Correspondence; O.O. Notes. Six double-pages A to F.

This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

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.

This focusses on research done on Rev Edward Vere Hodge's headmastership, in particular teaching and support staff working then, and life at Oakham School in the late 19th century.

The Old Oakhamian Magazine, published in 1947. Contents: Editorial; Dedication of the War Memorial; Marriages, Births, Obituaries; War Memorial Fund; Golfing Society; O.O. Notes; Annual General Meeting; Old Oakhamian Fund; Notices. Two double-pages A and B.

A bound copy of several Oakhamian Magazines from 1938 to 1943.