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A print-out of a plan of the ground floor of School House how it was before 1858. It is believed that the item was used for research and published in 'The Story of Oakham School' by John Barber.

This file focusses on various items relating to the history of Oakham School, its pupils and Old Boys, under the headmastership of Rev William Spicer Wood.

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

This file contains various plans of the buildings of School House and Old Hall.

This file contains various photographs of School House and Old Hall throughout the years.

This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

This collection covers the multitude of sports that pupils can do at Oakham School. Sports include cricket, rugby, hockey, athletics, netball and swimming as some of the richest in terms of items in the sub-series.

Most sub-series have a good photographic record of first teams, alongside comprehensive fixture and team lists. Some sub-series will contain correspondence, programmes and administrative documents.

There is an extensive collection of trophies and shields awarded to pupils and Old Oakhamians for their sporting achievements.

A collection of material which focuses the school accounts and financial procedures over the years. This includes information on general accounts, pupil fees, committee minutes, staff wages, legal proceedings, and guidance policies for staff.

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.