The area covered by the street lay outside the walls of Roman Eboracum, but it was occupied during the Viking Jorvik period, with various archaeological finds dating from the era.

In the Medieval period, the area was principally residential, the houses lying on Middle Water Lane and Friargate.

In 1892, a building was opened to house the city' police headquarters and main fire station.

[5] Nikolaus Pevsner described the street as "all of a piece with a series of striking red brick buildings in a variety of styles".

[2] Notable buildings on the west side of the street include 12 Clifford Street, the former York Institute of Art, Science and Literature, designed by Walter Green Penty; the York Magistrates' Court, designed by Huon Matear; and Clifford Chambers, a block of shops and offices which now includes an entrance to the Grand Opera House theatre.