The school opened in 1841 as a Church of England foundation and is known for its linguistic, military, and sporting traditions.

Two Cheltenham residents, G. S. Harcourt and J. S. Iredell, founded the college in July 1841 to educate the sons of gentlemen.

The plan to establish a "Proprietary Grammar School" had been agreed at a meeting of residents at Harcourt's home on 9 November 1840.

Accepting both boarding and day boys, it was divided into Classical and Military sides until the mid-20th century.

The 1893 book Great Public Schools by E. S. Skirving, S. R. James, and Henry Churchill Maxwell Lyte contained a chapter on each of what they considered England's ten greatest public schools; it included a chapter on Cheltenham College.

Cheltenham College has an affiliate tri-service Combined Cadet Force which has a history dating back to 1862.

[10] Eddie Butler, former Welsh, Barbarian and British Lions International Rugby player, taught French at the school.

Chris Stout won the Foster Cup (the individual championship for public schools) at Queen's Club in December 2011.

The full list of past principals and heads is contained in Cheltenham College Who's Who 5th edition, 2003, and is as follows: