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This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

This file focusses on photographs dating from the second half of the 19th century, under the Headmasterships of Mr Tabraham and Rev Fitch.

A fees book recording fees paid by pupils from Easter term 1876 to Christmas term 1879, including personal information such as parents' an guardians' names, addresses, age, entrance and registration fees and lessons chosen.

A copy of the 1881 British Census for Oakham School, including names, ages, birthplaces, family and current addresses. Eight pages A to H.

A photograph of a boys' Cricket 1st XI. Date '1887' is written (modern addition) but does not coincide with names of the pupils on the photograph and their leaving year. Date is now thought to be in 1882 or 1883, according to cricket records, even if some names do not match. Some names written on the item are not on the register and have been amended below in 'Access Points'.

A receipts book recording payments, brought over/forwards and school's balance from Summer term 1875 to Christmas term 1883.

This series focusses on the headmastership of Rev Robert Tabraham (1875-1878) and of Rev Henry Walter Fitch (Acting Headmaster, 1878) and contains items relating to the life at School in the second half of the 19th century.

This file focusses on reminiscences of life at Oakham School in the second half of the 19th century.

Research on Rev Vere Hodge era by John Barber, with some extracts from the Oakham School Magazines in 1884 and 1885, and hand-written notes. Three pages A to C.

Oakham School Magazine, recording the Spring term 1885 (published in Summer term 1885). Contents: The Library - a Sketch; a Glimpse of the Roman Wall; Oakhamienses in Cantabrigia; Six hours at Bettws; Wensleydale - Yorkshire; Poetry; The Last Evening; The Debating Society; The Athletic Sports; The Paperchase; Football; School Notes. Nine double-pages A to I.