The square was first established in 1801, around Town End Field owned by Thomas Winckley, as an exclusive residential area for the town's gentry. It is now occupied mostly by insurance, legal and other business offices, although some residential developments have recently been made. The square's gardens, now an open public park, originally consisted of private plots, each owned by a resident. A statue of Sir Robert Peel stands on one side of the central gardens opposite Cross Street, erected in 1852.
An Italian-style villa was built in 1850 on the south corner of Cross Street (number 11), which was later used as a County Court office from the 1940s. It was demolished in 1969. On the opposite corner (number 10) was the Winckley Club, a gentlemen's club, and next to it, in Cross Street, the Literary and Philosophical Institution (later called Dr Shepherd's Library and Museum), both built in 1846 and both now demolished.
Winckley Street lies between Winckley Square and Preston's main street of Fishergate.
Winckley Square has been the home of several schools.
Preston Grammar School 
Preston Grammar School dated back to the 15th century. In 1841 it moved to new premises in Cross Street next to the Philosophical Institution. In 1913 it relocated to Moor Park, and closed in 1967. It is not to be confused with the former Preston Manor County Grammar School in London.
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- Frederick Banister, civil engineer, Chief Engineer of the London, Brighton and South Coast Railway 1860-1896
- Lawrence "Lawrie" Bond, designer of the Bond Minicar
- Geoffrey Drain CBE, General Secretary of NALGO from 1973–83
- Sir Ronald Ellis
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- Sir John Eldon Gorst, Conservative MP for Chatham from 1875–92 and Cambridge University from 1892-1906
- Sir John Holmes GCVO CMG, Ambassador to France from 2001-7 and to Portugal from 1999-2001
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Preston High School 
Preston High School for Girls once occupied 5 Winckley Square. It was superseded in 1907 by the Park School for Girls, which educated younger girls in Winckley Square and older girls in Moor Park Avenue. It closed in 1967.
Preston Catholic College 
Preston Catholic College was a Jesuit school for boys, which began in 1865 in a house in Mount Pleasant (a narrow passage between the Square and Mount Street). In 1879 it moved to 29 Winckley Square and expanded over the next century until, at its peak of 915 pupils in 1970, it occupied the whole of the west side of the square from the northwest corner (number 34) as far south as Garden Street (number 25), with the exception of numbers 29 to 32. Classrooms, science laboratories and a swimming pool were built along neighbouring Mount Street in the 1930s. A gymnasium in Garden Street opened in 1970. The college also possessed extensive playing fields one mile (1½ km) south of the college, to which boys walked via the Old Tram Road.
The introduction of comprehensive schools in Lancashire forced the school, which had become a direct grant grammar school, to stop admitting under-16 pupils from 1978. In that year, its sixth form merged with the sixth forms of the other two Catholic direct grant grammar schools in Preston, namely Winckley Square Convent School and Lark Hill House School, to form Cardinal Newman College. Initially the Winckley Square sites continued to be used, but by 1986 the new college was concentrated at the Lark Hill site. Some of the Mount Street buildings have been demolished. The buildings on Winckley Square are used as offices. However the gymnasium and playing fields are still used by Newman College. A blue plaque commemorates the college at its original entrance, number 34.
Alumni include television football pundit Mark Lawrenson; Chief Associate Director of the Royal Shakespeare Company, Gregory Doran; author of The Wardstone Chronicles Joseph Delaney; creator of the Bash Street Kids and Minnie the Minx Leo Baxendale; and Archbishop of Liverpool Patrick Kelly. The 1950s footballer Eddy Brown taught at the school after his retirement from the game.
In 2010 the school was being sued by a former pupil over allegations of abuse.
Winckley Square Convent School 
In 1875, the Society of the Holy Child Jesus formed a girls' convent school from the merger of its three convent schools, St. Walburge's of 1853, St Mary's of 1871 and English Martyr's of 1871. The new school was at 23 Winckley Square, the former home of Thomas Batty Addison, once the Recorder of Preston. As the school grew, it came to fill the whole block between the streets of East Cliff and Garden Street, reaching a peak of 850 pupils in 1962. In 1978 it suffered the same fate as the neighbouring Catholic College, the site closing in 1981. The buildings are now used as offices and a Paul Heathcote restaurant.
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