The name 'Gosford' originates in a ford crossing the Sherbourne (the 'Goose-ford' over the 'Shire-stream'). This was located on the important east-west street through the historic town of Coventry. As the medieval town expanded, it spread in all directions, but especially along this route. Gosford was originally the name of the street on both sides of the ford. Sometime in the 13th century two bridges were built, one over the Sherbourne and the other over a 'leat' or 'race,'  an artificial channel running to a water corn mill situated on what is now Gulson Road (see water wheel plaque on Gulson Road fixed to Callice Court student halls of residence). An important event was the construction of the town wall and Gosford Gate in the late 14th century. As a result Gosford Street was divided into two and the part outside the wall became a classic medieval 'extra-mural' suburb.  The bridge nearest the gate was called 'Callice', named after the portcullis in the gate. This was corrupted to 'Calais' and local sense of humour led to the other bridge being called 'Dover' bridge. The Shearman and Taylors' Guild were forced out of the town by the more powerful merchant guilds and, in the early 15th century, constructed their chapel immediately outside the wall and partly on its own stone arch over the Sherbourne (see plaque on wall outside the tyre depot).

A hermitage was established in the early 15th century, which either replaced or converted into the chapel of St Margaret. By 1647 the chapel had been converted into a tithe barn and the few fragments that survived into the early 19th century disappeared by the 1850s (see plaque on the ground in St Margaret's Garden).

In the 16th and 17th century the street declined, along with much of Coventry, and houses were demolished due to lack of tenants. The Civil War left even more gaps in the street as buildings immediately outside the gate were pulled down to provide a line of fire from the town defences. The ditch that provided extra protection was found and excavated in 2006.

Speed's map of Coventry c1610 shows the street with complete building frontages, but Bradford's map, 1748-9, clearly indicates the gaps that had been created. It was only in the 19th century that the frontages began to be re-built in the gaps and in late that century Far Gosford Street became a shopping street for the first time. Previously, the buildings were almost exclusively dwellings intermixed with a few barns.