1866: Wellesley can trace its history back to 1866, when the school was established under the name of Conyngham House and was sited in Ramsgate.
1898: The present main school building was constructed, and just before the First World War it was bought by the then Headmaster Shirley Russell, and partners Herbert Day and Leonard Moon (the international cricketer and footballer), who were both killed in the war.
1928: John Boyce joined the school as a partner.
1939: Due to the Second World War, John Boyce, supported by Billy Williamson oversaw the evacuation of the school to three hunting lodges in Rannoch, Scotland. During this time the Army took over the school buildings.
1946-1964: The evacuees returned, and John Boyce continued as Headmaster, supported by his wife Barbara. They were supported by partners John Brooker and John Blackwell until 1964, when Bill Sale was appointed assistant headmaster and moved into the school with his wife Tessa and their family.
1966: The school became a Charitable Trust.
1968: Bill Sale became sole Headmaster, supported by his wife Tessa.
1969: The school was amalgamated with St Peter’s Court another local prep school and, thanks to the generosity of the Ridgeway family the current Junior School, the Old Hall and the Chapel were built. Four years later, the classrooms and corridor linking the Chapel and the old part of the school were completed.
1977: The Orchard was bought from the Boyce family and converted into a boarding house for girls, and the school became co-ed. Over the next decade the sports hall, music and art block were added and the swimming pool was rebuilt.
1990: Bill and Tessa Sale retired and were succeeded by Richard and Judith Steel. The Steel’s tenure saw the construction of the Centenary building incorporating science laboratories, design and information technology and carpentry workshop. Richard and Judith retired in 2006.
2006: Simon O’Malley was appointed Headmaster, supported by his wife Katy. Over the next 11 years Simon and Katy oversaw the continued development and success of the school until 2017.
2017: Gavin Franklin took over as Headmaster in September, and with his wife Claire is now leading the school into its next phase. The Pre-Prep department, located in Junior House, was opened in September 2019; allowing the school to open up a world of possibilities to children from the age of 3.