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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 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.

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.

A letter and booklet on the Humf Letters. The letter is to Dr. Spence from Colin Edgar about the project. The booklet contains information about D. H. W. Humphrey's life and the letters that he wrote to Betty Dawes.

Script of "The Humf letters", Humfrey's letters to Aunty Betty; 6 pages

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

This series relates to the History of Shooting at Oakham School. The collection is made of team photographs, score books and ephemera relating to successes at Bisley. The collection spans from the 1950s to 1980s.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

This sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

This series focuses on the history of the organs in the School Chapel, from the first one installed in 1930 to the current instruments built in 1993.