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The ruin of St. Oswald's Priory is the oldest surviving structure above ground in Gloucester. The priory was originally built as a minster by Aethelred and Aethelflaed, Lord and Lady of the Saxon kingdom of Mercia. Whilst the earliest documentary evidence dates to the 12th and 14th centuries, archaeological evidence supports an original build date of the late-9th or very early-10th century. The building was much altered in the centuries following its original construction; the arches of today's ruins are 12th and 13th century, but the wall still contains some of the Roman stone recycled by the Saxons in the original construction.

The minster was initially dedicated to St. Peter, as was the older abbey founded nearby in 679 by the Saxon sub-king Osric, which would eventually become Gloucester Cathedral. Following a Saxon raid into Viking territory to the north in 909, the beginning of the Saxon conquest of midland and eastern England, the relics of St. Oswald, a 7th-century king of Northumbria, were translated to Gloucester, marking its importance as a Saxon stronghold, and the minster rededicated. When Aethelred died in 911, Aethelflaed continued as Lady of the Mercians until her own death in 918. Both were buried at St. Oswald's, further signifying Gloucester's place as a royal Saxon centre of some import.

St. Oswald's thrived in the century after its founding, but fell thereafter under the shadow of it's neighbour, the future cathedral. The construction from 1089 of the new Norman Benedictine Abbey of St. Peter, close to the site of Osric's abbey, resulted in St. Oswald's ceding some of its land to the rival abbey in 1100 and again in 1218, when the new abbey expanded. By this time, St. Oswald's had been reformed from a minster to an Augustinian priory.

Following the dissolution of the monasteries, St. Oswald's was dissolved in 1537 and sold into private ownership in 1540. With the church already in a ruinous state, the priory was largely demolished. Parts of the priory's domestic buildings to the south of the church survived, incorporated into a dwelling (later known as Priory House) which was subsequently used as a private school. Of the church, only the north aisle survived, converted into the parish church of St. Catherine. A century or so later, the church was already in a poor state of repair when it was damaged by Royalist artillery during the siege of Gloucester in 1643.

From 1655 work began on dismantling the church, it's stone being used to repair Westgate Bridge, London Road and Horton Road. Only the north wall of the church was spared, and it is this we see in the ruins today. Priory House was demolished in 1823 or 1824, and the priory's claustral buildings to the south of the church are today traced by kerbing laid into the ground.

Despite the loss of its church, the parish of St. Catherine survived, and the cemetery at St. Oswald's remained in use until c.1857. A new church building was constructed on the northern edge of today's public space at St. Oswald's in 1868. It was a short-lived structure, demolished in 1921 after completion of the new Church of St. Catharine (with slightly altered spelling) on the corner of London Road and Cheltenham Road in Wotton.