Beneath the current structure, which was completed in 1816, lie the layered remains of several earlier crossings, each built more or less on the bones of its predecessor. When the 1816 bridge was under construction, excavations revealed the foundations of earlier structures, including regularly laid stones set on a platform of oak timbers supported by small timber piles, a form of foundation typical of medieval urban bridge-building in waterlogged ground.

The oldest crossing on this spot was known as Ostmans Bridge, a Norse-era structure dating from the eleventh century, which appears to have consisted of a series of causeways extending out to the central channel of the river rather than a single continuous span. This was succeeded over time by further bridge foundations, and eventually by a four-arched stone bridge of unequal spans completed in 1428. That bridge had a specific institutional purpose: according to Gwynn and Hadcock, it was built to connect the Dominican Friary on the south bank, whose church had been consecrated in 1402, with its schools of St Thomas Aquinas on the north side of the river, where philosophy and divinity were taught. The bridge appears on John Speed's map of Dublin from 1610, labelled simply as the Old Bridge, by which point it had already been in use for nearly two centuries. It remained standing into the early seventeenth century before falling into disrepair and being demolished. A painting by William Sadler, dating to around 1810 and showing the Four Courts from Merchant's Quay, captures the four-arched medieval structure still in place, shortly before it was pulled down to make way for the current crossing.

Father Matthew Bridge itself is unremarkable to look at, which is part of what makes the depth of history beneath it easy to overlook. It sits between Church Street Bridge to the north and the Ha'penny Bridge to the east, and can be crossed on foot from either quay. Nothing marks the site as the oldest bridging point on the Liffey, so the interest here is largely imaginative, a matter of standing on a busy Dublin crossing and knowing that the impulse to bridge this exact stretch of water goes back to the Viking city.