It was originally part of an ancient trackway that was paved by the Romans and used by the Anglo-Saxons who named it Wæcelinga Stræt (Watling Street).

In the 16th century, St Thomas-a-Watering on Old Kent Road was a place where religious dissenters and those found guilty of treason were publicly hanged.

In the 19th century, it acquired the name Old Kent Road and several industrial premises were set up to close to the Surrey Canal and a major business, the Metropolitan Gas Works was developed.

[5] The Inter III was one of the most important Roman roads in Britain, linking London with Canterbury and the Channel ports at Richborough (Rutupiae); Dover (Dubris) and Lympne (Lemanis).

[12] Charles II's journey along the road on his way to reclaim the throne in May 1660 was described by contemporary writer and diarist John Evelyn as "a triumph of about 20,000 horse and foote, brandishing their swords and shouting with inexpressible joy".

[1] St Thomas-a-Watering became a place of execution for criminals whose bodies were left hanging from the gibbets on the principal route from the southeast to London.

On 8 July 1539, Griffith Clerke, Vicar of Wandsworth was hanged and quartered here along with his chaplain and two others, for not acknowledging the royal supremacy of Henry VIII.

[13] The Welsh Protestant martyr John Penry was also executed here on 6 April 1593;[14] a small side street nearby is named after him.

[15][16] In the early-18th century, the Rolls family of The Grange in nearby Bermondsey acquired a significant amount of land around Old Kent Road.

[17] The main road route gave rise to ribbon development because of the increasing urbanisation of the expanding metropolitan area.

In the early-20th century, social housing was built on land previously held by the family who gave away their interests for public benefit including the library at Wells Way in Burgess Park, the girls grammar school at Bricklayers Arms (St Saviour's and St Olave's School) and the Peabody Estate (Dover Flats and Waleran Flats).

Expansion of the gas works in 1868 required the demolition of Christ Church, Camberwell, which was built in 1838 and rebuilt on the opposite side of the road by Livesey.

[26] During the 19th and 20th century, the industrial and working class makeup of Old Kent Road made it a haven for organised crime and violence.

Lennox Lewis' manager Frank Maloney grew up in the area and recalled, "If you weren't into crime, people thought you were a pansy".

Henry Cooper trained in the boxing club above the Thomas a Becket pub from 1954 to 1968; he unveiled a local blue plaque there in 2007.

Unlike many places in London, the Old Kent Road area did not suffer significant bomb damage during World War II.

[36] In 1968, a flyover opened at the northern end allowing access to New Kent Road which catered for the main flow of traffic.

279 opened in 1856 and was well known as a gin palace, and later became a champagne bar and featured DJs such as Steve Walsh and Robbie Vincent.

[41] The World Turned Upside Down had been on the Old Kent Road since the 17th century, and may have been named after the discovery of Australia, Van Diemen's Land, or Tierra del Fuego in South America.

[46] This master plan would mimic similar regeneration projects in other London neighbourhoods such as Elephant & Castle,[47] Nine Elms and Canada Water.

In Charles Dickens' David Copperfield, the titular character runs down the road trying to escape from London to Dover, though in the narrative the street is still partly rural in nature.

[55] It is featured in the chorus of the Levellers' song "Cardboard Box City", which criticises the slow action on helping the homeless in London, specifically Old Kent Road being infrequently visited by the wealthy due to its being south of the Thames.