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 School list of staff and pupils for the Summer term 1902. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1901; Oxford & Cambridge Board, 1902; Royal Drawing Society. Five double-pages A to E.

A roll call for School House, Mr. Scriven's, Mr Williams', Bank House and the Day Boys in Winter term 1887. One name has been hand-written in Form VI.

An inventory an valuation of furniture, fixtures and effects in and upon the premises known as 'Junior House', made for transfer from E. Pickering Clarke to the Trustees. Contains information on the building, its fixtures and fittings, in the dining room, kitchen, garden, toilets, pantry, sick room, matron room, dormitory, study, classroom, bathrooms, coal house, workshop, tool shed, gardens and tennis nets. Thirty-three pages A to AG.

A prospectus promoting studying at Oakham School in 1897. Contents: Trustees & Staff; Subjects; Upper School & Lower School; Examinations; Boarding Houses; Library, Games & Extras; Terms; Holidays; Infectious Disease; Scholarships, Exhibitions & Prizes. Three double-pages A to C.

A School list of staff and pupils for the Summer term 1903. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1902; Oxford & Cambridge Board, 1903; Royal Drawing Society. Five double-pages A to E.

A prospectus promoting studying at Oakham School in 1902. Contents: Trustees & Staff; Subjects; Upper School & Lower School; Examinations; Boarding Houses; Library, Games & Extras; Terms; Holidays; Infectious Disease; Scholarships, Exhibitions & Prizes. Three double-pages A to C.

A roll call for School House, Mr. Scriven's, Mr Williams', Bank House and the Day Boys in Winter term 1887.

A prospectus promoting studying at Oakham School in 1903, with illustrations. Contents: Brief History; Subjects of Instruction; Boarding Houses; Health; Games; Holidays.

A School list of staff and pupils for the Summer term 1901. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1900; Oxford & Cambridge Board; Drawing Examination. Five double-pages A to E.