During 2018, the Clwyd Powys Archaeological Trust carried out an archaeological watching brief during groundworks for a housing development on land to the west of Upper Church Street in Oswestry. This followed earlier work which involved as desk-based assessment of the Development Area and an archaeological evaluation. The watching brief revealed a single feature of medieval date, located at the north-eastern end of the southern block of housing, and some evidence of later features which collectively corresponded with the evidence provided by the evaluation. These features are thought to be related to the occupation of houses located along Upper Church Street, though the area of the northern block of housing, nearest to the street frontage, was devoid of comparable features, probably owing to disturbance from the construction of a modern house that was extant in 2015 but had been demolished prior to the commencement of the watching brief.