[1] They share a common badge design (and a strong rivalry), but while Uppingham's colours tend towards blue and white, Oakham's are black and red.

Johnson received an income from four church positions and used this wealth to set up a number of charitable institutions, including the two free grammar schools at Oakham and Uppingham.

The original school building was restored in the eighteenth century and remained the sole classroom for 300 years.

In 1749 a case involving payment of rates recorded that "the school of Uppingham is not nor hath been of equal repute with that of Oakham.

[6] Even so, numbers attending were well below 50, and while Uppingham flourished in the second half of the nineteenth century, Oakham did not to the same extent.

New facilities for science teaching were created, boarding accommodation was improved with new building and extensions, and then a new school house was built.

He and the Rutland Local Education Authority did not agree on the possibilities of re-organisation of Rutland's schools, and as a result in 1970 the school (then 700 in size, all boys) reverted to full independence from the local authority, and in 1971, Oakham admitted female pupils for the first time, with the intention from the beginning of being co-educational throughout.

[8] In 1984 the quatercentenary of the school was celebrated by a visit from Queen Elizabeth II and Prince Philip, Duke of Edinburgh.

During their time in the lower school, pupils study all of the core subjects (mathematics, English, science, history and geography) as well as French and either German or Spanish, religious education, Latin, Design & Technology and ICT.

There is also a carousel system of creative and performing arts courses, which include textiles, 2D art and sculpture, and a separate carousel for drama and dance, and pupils take part in a physical education scheme of swimming and general ball skills.

Pupils then choose two subjects from a selection, including a second foreign language, drama and theatre studies, Textiles, Painting, Sculpture, Design & Technology, sports science and a combined Greek and Latin course.

The day houses are located at the north end of campus, in the grounds of the former Oakham Workhouse, later Catmose Vale Hospital.

The Girls transitional boarding house, Stevens, is located alongside the boys counterpart, Wharflands, in the center of the campus.

The boys full-boarding houses Chapmans and Haywoods are on Kilburn road ( the western-most part of the campus) Oakham offers both the International Baccalaureate (IB) and AS/A2 levels.

Prior to 2003 Leicestershire County Cricket Club occasionally played games on the school grounds.