Uppingham has a musical tradition based on work by Paul David and Robert Sterndale Bennett.

Despite its small size, pupils then regularly gained places and scholarships to Oxford and Cambridge universities.

One of the earliest Old Boys to gain fame was Thomas Bonney, a pupil in the 1850s, who became the most distinguished geologist of his time, and president of the Alpine Club.

During his headship on 4 April 1876 the entire school, consisting of 300 boys, thirty masters, and their families, moved temporarily to Borth in Wales after an outbreak of typhoid ravaged the town as a result of the poorly maintained water system.

In Borth the school took over the disused Cambrian Hotel and a number of boarding houses, remaining there for fourteen months.

At a time when mathematics and classics dominated the curriculum, he encouraged many ‘extra' subjects: French, German, science, history, art, carpentry, and music.

He opened the first gymnasium in an English school, the forerunner of the present sports hall, and later added a heated indoor swimming pool.

He commissioned a number of buildings, notably the chapel designed by the Gothic Revival architect G. E. Street.

Ernest William Hornung was at the school in the 1880s; he wrote several novels but his fame rests upon his creation of the character A. J. Raffles.

Pupils have continued to go on to later fame – Patrick Abercrombie, pioneer town planner; Sir Malcolm Campbell, motor racer; James Elroy Flecker, poet and playwright: C. R. W. Nevinson, official war artist in both world wars; W. H. Pratt (Boris Karloff), film actor; E. J. Moeran, composer; Lt General Sir Brian Horrocks, Commander of the XXX Corps under Montgomery, and later a TV lecturer on battles and war; and Percy Chapman, captain of the England cricket team 1926–30, who won the Ashes.

New squash courts were built and in 1970 the sports centre, incorporating the old swimming pool, was opened, with the later addition of a climbing wall and a weights room.

In the post-war period, sports other than the main ones of rugby, hockey, cricket, athletics, swimming and shooting began to be introduced including tennis, basketball, badminton, fencing, squash, sailing, soccer and golf.

In 1945 Douglas Guest succeeded Robert Sterndale Bennett as Director of Music and this area of school life developed further.

A new choir division appears high on the south wall, and a new console and action have been installed, along with new pipework.

The organ is notable for a smooth Harrison tone and a rare pair of independent sets of Swell shutters – one opening west into the nave extension and one south across the repositioned choir stalls.

Uppingham has one of the largest private theatres in the country, in a building based on the original Leipzig Gewandhaus.

She wrote to John Vickers, the OFT director-general, saying, "They are not a group of businessmen meeting behind closed doors to fix the price of their products to the disadvantage of the consumer.

[8] In March 2011, twice Olympic gold medallist Sebastian Coe officially opened the school's new sports centre.

The Li House is based in what used to be the Thring Centre and is named after Dr the Hon Sir David Lee Kwok Po, a pioneering OU who was the first Uppinghamian from Hong Kong in 1954.