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This sub-series focusses on team photographs of cricket teams since 1860, first teams as well as second XI and junior teams.

A ledger of O.O. Charles Scott, Tailor of Mill Street, Oakham relating to trade with Oakham School from 1860 to 1870.

A photocopy of an article from The Daily Courier of Liverpool reporting a case of Libel in 1863 opposing O.O. Padley and Cooper; Oakham School is mentioned a few times.

A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

This file focusses on photographs on the School Campus throughout the years. Some photographs are of the whole campus, in particular aerial photographs taken by Aerofilms Ltd, and some are collection of individual buildings, taken by Companies or individuals.

This file focusses on official reports published on the life at Oakham School in the 1860s.

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

This collection focuses on the administrative side of the school including admissions and trustees.

There is a rich collection of admissions books dating back to the 19th century alongside detailed notes of Trustees' committee minutes and development plans.

School inspections undertaken by external bodies are represented in this sub-fond and include some of the 19th century schemes which helped to found the school as one independent from Uppingham.

ADM/4 contains policy documents outlining the health and safety measures in the school.

A book compiling the minutes of the Trustees' Financial Committee meetings.

This series relates to the Finance Committee of the Trustees, in particular minutes of their meetings.