The Bullring, roughly 30 metres by 20 metres and entered from four sides, with Main Street running through it to the north and south, was once the site of organised bull baiting, a practice so embedded in the butchers' trade that it was written into law. In 1621, the Corporation of Wexford granted a charter to the Fraternity or Guild of Butchers permitting them to regulate their trade, on the condition that they stage two displays of bull baiting each year: one on the feast of St Bartholomew, the 24th of August, and one at Hallantyde, the feast of All Hallows at the start of November. After each event, the hides were to be presented to the mayor. The practice was not purely theatrical; the baiting and stressing of animals was understood at the time to tenderise the meat, and it is likely that baiting had been going on in the square well before the charter formalised it. It continued until at least 1770, and possibly as late as 1798, when regulations against public assemblies finally brought it to an end.

The square has seen considerably darker events than the baiting of livestock. On 11th October 1649, Cromwell's forces broke into Wexford town and met fierce resistance when they reached the marketplace. Cromwell described what followed in a letter to the Speaker of the English Parliament: 'our forces brake them, and then put all to the sword that came their way.' A petition submitted by the townsmen in 1660 recorded that women and children were among those killed. The square also had a brief identity crisis in the 1790s, when the Marquis of Ely installed a fountain at its centre, prompting locals to rename it Fountains Square. The fountain was relocated to the Cornmarket around 1800, and the older name came back into use. The eastern side of the square was once occupied by the Tholsell, a courthouse typical of medieval Irish market towns, which has since been replaced by twin Victorian market houses built around 1870.