The earliest known alumnus to be connected with Canada was William Alexander, 1st Earl of Stirling (c 1577-1640), who having been tutor to James VI's son Prince Henry, was granted a charter for the settlement of a large area of America known as "Nova Scotia" by King Charles I. Although his attempts to settle the land with Scottish settlers failed, and the land was later ceded to France, the Scottish connection would remain a constant throughout Canada.

By the eighteenth century Scottish alumni of the University emigrated in increasing numbers to Canada. Among the earliest were alumni engaged in all sectors of society from the military to trade, medicine to religion, and politics as communities settled and made Canada their new home. This emigration to Canada had an enormous impact on education at all levels, with Scottish clergy contributing or founding village and town schools. Their impact on university education became particularly significant. Until the 20th century nearly half the institutions of higher education had Scots involved in their founding, and the curricula of the oldest were all built around the common sense school of philosophy crafted by Glasgow's Thomas Reid, Professor of Moral Philosophy at the University from 1764 to 1781, and a key figure in the "school of common sense philosophy" which flourished during the Scottish Enlightenment.

McGill University was founded in 1821 with revenue from the estate bequeathed by James McGill, an alumnus of 1756. He had emigrated to Canada before the American Revolution, and was engaged as a fur trader and then a merchant in Montreal. The Reverend Thomas McCulloch who studied arts and medicine in the 1790s, went to Nova Scotia in 1803 and had a profound influence upon higher education there. He founded Pictou Academy and became the first President of Dalhousie University.

Likewise, Canadian-born students with links to Scotland soon returned to contribute to the growing educational sector in their home country. George Monro Grant (MA 1857, DD 1878) was a Nova Scotian of Scottish origin, who was principal of Queen's University in Kingston, Ontario, from 1877 until 1903 turning it into a University of strength from its establishment in 1841.

By the early-nineteenth century Scots born in Canada began to return to the University, and by 1965 over 450 Canadian students crossed the Atlantic to register for study at the University of Glasgow; the first Canadian student was Andrew Mitchell who attended in 1796. He was born at ‘Upper Canada’, now part of the state of Michigan in the USA, son of a Scottish father who worked as a physician and fur trader, and a mother of Indian extraction. Other sons of tradesmen born in Canada followed, such as John Russel, the son of the founder of John Russel & Co, merchants in Montreal who returned to his father’s birth country to study. Russel Metals Inc. grew out of the family business and today is a leader in the metals distribution business in North America.

In the class register of James Jeffray, Professor of Anatomy and Botany at the University and a renowned surgeon, 16 students of Canadian origin are recorded. New Brunswick-born friends,

From these earliest connections, generations of Scottish-Canadian families began to attend the University, such as the Anderson family. Dr William Anderson, MBChB 1867, of Heart's Content, New Foundland, was the first of three generations to study medicine at the University.

Both countries continued to inspire each other not only in medicine, but in the arts and sciences. The novelist and diplomat, John Buchan (1875-1940), was an Arts student in the 1890s, and published poetry and essays in the Glasgow University Magazine. He was awarded an LLD in 1919, and after serving as MP for the Scottish Universities from 1927 to 1935, he was appointed Governor-General of Canada from 1935-40. The Scottish-Canadian poet and writer Robert Service (1874-1958) also matriculated for an English class in 1893, and emigrated to Canada at the age of 21 where he would become known as "the Bard of the Yukon".

Increased mobility during the twentieth century also enabled Canadian alumni of Glasgow to contribute further afield. Anstruther Abercrombie Lawson lectured at the University in Botany between 1907-10 while undertaking postgraduate study, and after graduating DSc was subsequently appointed the foundation Professor of Botany at the University of Sydney. The first female student and graduate from Canada was medical graduate Honoria Somerville Keer (1883–1969), MB ChB in 1910. Born in Toronto she served in her capacity as a medical officer around the world.

Another Canadian-born alumnus in 1879, Andrew Bonar Law (1858-1923) not only became Rector of the University (from 1919 to 1922), but Prime Minister of the United Kingdom from 1922 to 1923.

During the widespread unrest within Europe of the twentieth century and increased mobility, the University of Glasgow provided an educational haven to many migrants, who in turn continued on their immigration westward onto Canada where they made marked contributions, particularly in the field of Science. In some cases, it was at the University of Glasgow where they met their partners, with whom they immigrated to Canada, such as Polish-born Maria Kolasa BSc 1946 and PhD 1949, who married a fellow University of Glasgow student, Wacław Przybylski and they moved together to Canada where Przybylska was appointed to the National Research Council of Canada's Division of Applied Chemistry.

The stories of these historic alumni are individual and varied but all with the same strong Canadian-Scottish connections and tradition of educational exchanges, which continue between the countries. The University continues to maintain and develop these important historical links, and is currently setting up a Scottish-Canadian Studies Program.