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This sub-series focuses on photographs of girls, living in Round House since its inception, as well as well Leavers photographs of both School house and Round House pupils since the 2000s.

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 collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

A photograph of staff leavers and their wives in 1999.

The Oakhamian Magazine, recording the Winter term 1996. Contents: History; Gap Years; Art; Languages; Miscellany; English; Drama; Performing Arts; Sport; Science; Houses.

The Oakhamian Magazine, recording the Summer term 1997. Contents: Farewells; Jerwoods Activities; Languages; Science; Art; Sport; Geography; Miscellany; Performing Arts; Houses; Miscellany.

The Oakhamian Magazine, recording the Summer term 1998. Contents: Editorial; Speech Day; Leavers; Music; Drama; Belize; Namibia Expedition; Art & Design; Design & Technology; Trips; Sport; House Reports; The Chapel Choir.

The Oakhamian Magazine, recording the Winter term 1998. Contents: Editorial; Chapel; Music; Drama; Art; Design & Technology; Short Stories; Trips; Now and Then; Sport Tour to South America; Sport; House Reports; Seventh Form Leavers '98.

The Oakhamian Magazine, recording the Summer term 1967 (published in Winter term 1967). Contents: Editorial; School News; Avete; The Term now Standing; Music; Around the Societies; Face to Face; Travellers' Tales; Comment; Drama; Poetry; Games; The Combined Cadet Force; Shooting; Scouts; Letters to the Editor; O.O. News; University Entries; Valete.

A bound copy of several Oakhamian Magazines from 1964 to 1967. Item A has a black cover; item B has a brown cover.