- Oakham School was founded in 1584 by Archdeacon Robert Johnson, who was also the founder of nearby Uppingham School, and today the two institutions share an intense rivalry. In 1971, Oakham accepted both girls and boys throughout the school, and in 1995 it became the first public school to go online.
- Nothing captures the atmosphere of the school better than the day its first XV rugby team was crowned National Schools’ Cup champions at Twickenham in 2023 – a match attended by more than 1,000 pupils, staff, parents and Old Oakhamians. Beyond sport, Oakham has a strong extracurricular programme, with interest groups spanning Model UN, sailing, cooking on a budget and yoga.
- A team of 30 staff oversee the PSHE programme. Weekly sessions are held to help pupils focus on their wellbeing and the medical centre has three mental health professionals. Alongside A-levels and GCSEs the school offers BTecs and the Extended Project Qualification.
- Scholarships carrying a small fee reduction are offered as well as means-tested bursaries. The Continuity of Education Allowance is available for military families.
- Alumni of the school include the comedian Miles Jupp and the former England cricketer Stuart Broad.
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