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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.

A School list of staff and pupils for the Summer term 1902. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1901; Oxford & Cambridge Board, 1902; Royal Drawing Society. Five double-pages A to E.

A roll call for School House, Mr. Scriven's, Mr Williams', Bank House and the Day Boys in Winter term 1887. One name has been hand-written in Form VI.

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.

Order of service for a memorial service for Walter Lee Sargant in the School Chapel on 22 September 1956.

Old Oakhamian Calendar, published in 1921. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1920; Letter from the Headmaster with plan; Old Oakhamian Notes; Old Boys' Matches. Six double-pages A to F.

Old Oakhamian Calendar, published in 1924. Cover with contents: Editorial; List of Addresses of Members of the Old Oakhamian Club - 1924; Meeting of Old Oakhamian Club; Old Oakhamian Luncheon; A Letter from the Headmaster; Cambridge Letter; Officers' Training Corps; A Weekend in Africa; Births, Deaths and Marriages; Old Oakhamian Matches; School Staff - September 1924. Nine double-pages A to I.

The Old Oakhamian Magazine, published in 1933. Contents: Annual Dinner; Cricket and Football; The Golfing Society; The School, 1932-1933; Births, Deaths and Marriages; O.O. Notes; Notices; Football Fixtures, 1933-34. Two double-pages A and B.

The Old Oakhamian Magazine, published in 1934. Contents: Quinquennial Meeting; Annual Dinner; Cricket and Football; The Golfing Society; School Notes; Births, Deaths & Marriages; O.O. Notes; New Members; Notices; School Football Fixtures; Correspondence. Two pages A and B.

The Old Oakhamian Magazine, published in 1949. Contents: Editorial; Annual Meeting; Annual Dinner, 1949; Regional Meetings; The O.O. Fund; Golfing Society; War Memorial Fund; School News; Record of O.O. in the Forces; O.O. Notes; Obituaries; New Members; Changes of Address; Notices. Two double-pages A and B.