At the turn of the 20th century, a number of Hamilton’s Scottish-Canadian organizations organized politically for the establishment of a kilted regiment as a visible symbol of Scottish culture as it was understood. The movement’s leading figures were Presbyterians. Despite the initial opposition of the Liberal government, the 91st Highlanders were gazetted on 16 Sept. 1903. On that day, the Reverend Neil McPherson, minister of St Paul’s Presbyterian became the chaplain of the new Regiment. It was no mere coincidence. One of the founders of the Regiment and its first Commanding Officer, Lt-Col William Alexander Logie, was a leading member of the congregation. McPherson was succeeded as chaplain by the Reverend Doctor Daniel R. Drummond (1868–1931) on 2 Oct. 1905 and St Paul’s continued as the Regimental church.

There were annual church parades to the church, and the chaplains presided over the usual duties associated with a regimental chaplain: births, marriages, and deaths. In October 1928, the Regiment, on the occasion of its 25th anniversary, trooped a new set of Colours; its first set were laid up in St Paul’s, where they remain today. Three days after Drummond’s death, on 12 Oct. 1931, the Regiment had a new chaplain, Dr William Barclay of Central Presbyterian Church in Hamilton. After 28 memorable years at St Paul’s, the Regiment acquired a new Regimental church and chaplain, and its direct association with St Paul’s ended.