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 teaching staff photographs, since John Buchanan's headmastership. More recent photographs include both teaching and support staff.

A collection of documents, chiefly photographs, of Wharflands, purchased by the then Headmaster Walter Lee Sargant in 1920. The property was converted into a boys’ boarding house for twenty-six boys, while the Old Stables were used for other school purposes. Extension work began in 1928, adding four new dormitories and a large dining hall. The O.T.C. established its headquarters in the new extension. With the boys now living in the extension, the Housemaster and his family could occupied the old house. The first floor was converted into some classrooms, for the teaching of Science and Maths. In 1960 and 1977, a series of improvement and refurbishment work started and changing rooms were modernised, while new rooms were added.

This series focuses on Wharflands pupils and staff since its opening in 1920. Most of the series is made of house photographs, various photographs of Housemasters and administration documents.

Items related to Walter Lee Sargant's book "Oakham through the centuries".

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.

2 photographs of the unveiling of the plaque of the new Music School by Malcolm Williamson. Items A and B

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

An M.A. History dissertation by Holly Harrod on the school and it's relationship with the town.

Magazine named "The Old Oakhamian", on paper, stappled; 7 pages; contents: Editorial, Dedication of the War Memorial, Marriages, Births, Obituaries, , War memorial Fund, Golfing Society, O.O. Notes, Annual General Meeting, Old Oakhamian Fund, Notices