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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.

A5 magazine with a portrait of Father Louis Merton on the cover; 48 pages; contents: Annual Dinner 1993, Time for a Change?, This Year's President - On the Move, O.O. Dinners, O.O. Day, Reunion, School News - Round-up, Oxford and Cambridge Results, Chapel, OSCharities Association, Music, Drama, Duke of Edinburgh's Award, School Sport - our finest year?, Cate's China, Phil's Japan, Engagements, Marriages, Births, Deaths, Obituaries, O.O. News, O.O. Sports, O.O. Lodge, Club Colours, Addresses of Members, Half a Century Ago, Celebration of Rutland, Notices, Diary Dates; with a portrait of Corrina Pike, a photograph of the organ, a potograph of the Trustees 1993

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

Staff and Trustees list and school roll per forms, including successes at the Royal Drawing Society Exam and Oxford and Cambridge examinations. Items A to E

Staff and Trustees list and school roll per forms, including successes at the Royal Drawing Society Exam and Oxford and Cambridge examinations. Cover detached from the booklet. Items A to E

This file focusses on roll call lists from the early 20th century, under the headmastership of Walter Lee Sargant.

A roll call of the summer term including names of trustees, teachers, upper, middle and lower school, and prizes given out for subjects and awards. Items A to E

This file focusses on various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.

A prospectus including list of Trustees and staff. Contents: Subjects, Upper School, Lower School, Examinations, Boarding Houses, Library, Games, Extras, Terms, Holidays, Infectious disease, Scholarships, Exhibitions and Prizes. Items A to C

An edition of Matkin's almanack including a section on Oakham School on page 16.