In medieval times, Eastcheap was the main meat market in the City of London, with butchers' stalls lining both sides of the street.

The name is first attested on an Anglo-Saxon penny of King Harold I (reigned 1035–1040) that was minted in London by the moneyer Eadwold between 1035 and 1037.

Falstaff's famed tavern, which stood on the Great Eastcheap section of the road, was demolished at this time.

At 16 Eastcheap is the Monument branch of Citibank; this was the site of St. Andrew Hubbard church, where the economist Thomas Mun was baptised, but the structure was later destroyed by the Great Fire.

In 1834 they moved to larger premises in Fish Street Hill, at the western end of Eastcheap, now occupied by an exit of the modern Monument tube station.

During excavation of the site the foundations had stones that had the character of Roman workmanship, and Samian pottery was discovered.

The statue's exact origin is unclear, but the primary theory is that there were two construction workers working on either the Monument to the Great Fire of London, about 400 ft away, completed in 1677, or 23 Eastcheap itself, the office of spice merchants Hunt and Crombie, architected by John Young and Son, and constructed by Piper and Wheeler, completed in 1862, were sitting on a rail high up on the scaffolding eating lunch; one of them noticed that their cheese sandwich was mostly eaten, and blamed the other, who denied the allegation, so they got into a fight, and either they slipped or the rail broke, and both fell to their deaths.