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This series focusses on the headmastership of Henry Price (2019-today) and contains items relating to the life at School in the 2020s, its staff and pupils.

This series focuses on the Day girls' house of Hambleton, founded in 1997. The main items are informal photographs of house events and house diaries, planning and detailing the house routine throughout the years.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

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 Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

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.

Two letters between the Headmaster Tony Little and Ray Tyler regarding the development of cricket at Oakham School and the position of Cricket co-ordinator in 1999.

Two letters between the Headmaster Tony Little and Rosemary Goddard, sister of Geoffrey Brittlebank who dies in the Second World War, regarding visiting the War Memeorial.

Correspondence between HMC Schools regarding the Golden Jubilee in 2002.

2 letters between the Headmaster Tony Little and Michael Yeld regarding regarding Robert Norman Yeld's life at school and after and sending one of his drawings to the school