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This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

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.

A letter from Michelle Northcott, Housemistress of Lincoln House, to Parents and Guardians reviewing the 2017 Winter term's achievements and events.

A letter from Bertie Bowes, Housemaster of Wharflands, to Lynn Wilson informing him that he will be a house prefect next term alongside John Grenfell and explaining the responsibilities and duties of the prefects.

A letter (B) from General Sir Henry Ponsonby to James Hawthorn, acknowledging the receipt of the petition addressed to the Queen from the prefects of Oakham School on her 50th anniversary. And the original envelop (A), with seal and post stamps.

This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

This sub-series focuses on letters related to the history of Wharflands house, its pupils and staff.

This file focusses on letters and cards relating to Oakham School, sent/received under the headmastership of Rev Vere Hodge.

This series relates to Junior Boarding girls of Lincoln House. The house was built in 1974, as part of the new Jerwoods Campus for the Lower School. Most of the collection is made of the House photographs, as well as informal photograph of the girls in house events and sports competition, and programmes of some house events.