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.

A letter from the Headmaster Tony Little to Parents regarding the responses of a questionnaire sent to parents in 1997. Two pages A and B.

A staff handbook for the academic year 1996-1997. Twelve pages A to L.

A staff handbook for the academic year 2001-2002. Forty-nine pages A to AW.

A note from the Headmaster Tony Little regarding the history of the school, its location, academic performance and co-curricular activities, sports, and school life.

Information sheet detailing the times when pupils can go to the School Chapel for peace, quiet and prayer.

The Ancaster house diary for the years 1983 to 1989 with notes on the everyday life of the house, absences, house events, school information about the girls (Pastoral), letters to/from parents and house sports teams.

The Ancaster house diary for the years 1989 to 1998 with notes on the everyday life of the house, absences, house events, school information about the girls (Pastoral), letters to/from parents, house sports teams and results, programmes of house and school events.

The Ancaster house diary for the years 1998 to 2006 with notes on the everyday life of the house, absences, house events, school information about the girls (Pastoral), letters to/from parents and house sports teams and results, programmes of house and school events.

This collection focuses on the pastoral and medical care for pupils and staff at Oakham School.

This includes a sub-series donated by Jane Matthews, the first female deputy head of the school. Her collection contains minute and administrative documents relating to maternity leave, girl boarding and tutorials.

Particular strengths of the collection are the patient books in PMC/2. There are record collated by the sanitorium and subsequent medical centre, as well as accident diaries and medical administrative documents.