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This collection highlights the achievements of Old Oakhamians after they have left Oakham School.

Two photographs (A and B) of the O.T.C. contingent in 1916. One copy is mounted on a card board and names are written.

A prospectus for the school including staff list, trustees, the history of the school, information on the timetable, uniform, holidays, chapel, boarding, curriculum, Libraries, games, admission, scholarships, day boys and pocket money. Also includes several photographs of around the school, and a sketch of rugby players. Items A to R

Bound Copy of several Old Oakhamian Issues; red, hard cover

A prespectus from this year including trustees and teaching staff names, information on the school, fees, and scholarships availible.

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

A5 magazine, white cover with the badge of the school on the cover; 56 pages; contents listed on the inside cover: Editorial, This Year's President, Annual Dinner, Annual General Meeting and O.O. Day, Regional Meetings, School News, O.O. News, Engagements, Marriages, Births, Deaths, Obituaries, New Members, Address Changes, Masonic Lodge, Notices, Diary Dates, Rugby Fixtures, Golf, Rifle Club, Letters, R.G.H., Stop Press; with a portrait of P.I.D. James, a photograph of the O.O. Golfing Society

A prospectus for the school including staff list, trustees, the history of the school, information on the timetable, uniform, holidays, chapel, boarding, curriculum, Libraries, games, admission, scholarships, day boys and pocket money. Also includes clothes list, rules for the Old Oakhamian club, programme for speech day, admission form and note regarding photographs. Items A to O

A prospectus' for the school including staff list, trustees, the history of the school, information on the timetable, uniform, holidays, chapel, boarding, curriculum, Libraries, games, admission, scholarships, day boys and pocket money. Includes some photographs of the school; with a list of corrections inserted and an admissions form. Items A to C