[citation needed] Cleveland Street commences at its intersection with City Road in Chippendale and heads in an easterly direction as a four-lane, single carriageway road through Darlington, over the railway lines between Central and Redfern stations and east through Surry Hills, crossing the Eastern Distributor and South Darling Street, to eventually terminate at the intersection with Anzac Parade and Lang Road, Moore Park.

[3][4] Daniel Cooper purchased approximately five hectares (twelve acres) from Smith and built the heritage-listed Cleveland House in the early 1820s.

The decision in 1850 to build Redfern terminus brought industry to the area and resulted in the subdivision of many of the gentlemen's estates in the neighbouring suburb of Surry Hills.

Metroad 4 was later re-aligned along City West Link on its completion in 2000; Cleveland Street has remained without an allocation since.

Further east, between South Dowling Street and Anzac Parade, 2016 average traffic volumes peaked at 20,000 vehicles west-bound.