Hugh Stewart was born in 1884 in Aberdeenshire, Scotland. He won a scholarship to Fettes College, Edinburgh before continuing his education at Edinburgh University and Trinity College, Cambridge. After graduating from Trinity in 1907 he spent almost two years in Russia as a private tutor in the Paschkov family before returning to England towards the end of 1908. His time in Russia formed the basis of his book 'Provincial Russia' published in 1913. His book was also included in a larger volume on the country 'Russia' by G. Dobson, H.M. Groves and Hugh Stewart, also published in 1913. On his return from Russia, Hugh Stewart pursued an academic career, firstly at the University of Liverpool and then as Professor of Classics in the University of Christchurch, New Zealand. On the outbreak of the First World War, Hugh Stewart volunteered for service joining the New Zealand Expeditionary Force. Serving in the Gallipoli campaign and later on the Western Front he rose to the rank of Colonel, was mentioned in dispatches five times, and was awarded the Distinguished Service Order with bar, the Military Cross, the Croix de Guerre and the CMG. Following the war he was asked by the government of New Zealand to write the official history of the New Zealand forces during the conflict. This was published in 1921 as 'The New Zealand Division: A popular history based on official records'. Stewart returned to his post at the University of Christchurch in 1919. In 1926 he chose to return to England having accepted the position of Professor of Latin in the University of Leeds, later rising to become Dean of the Faculty of Arts.
In 1930 Hugh Stewart took up what was to be his final position as Principal of University College, Nottingham. At the time that Stewart became Principal the College was at a crossroads. Founded in 1877 with the aim of providing a university style education to the working and middle classes by 1930 it had found itself being overtaken by many newer institutions, which had managed to make the move from University College to full University. In 1928, two years before Hugh Stewart's arrival, the College made a concerted effort to gain its Royal Charter (the recognised way of establishing a new University). A large endowment fund was needed to realise this aim but despite a large publicity campaign the funds raised fell short of the necessary amount. On his arrival at the College as Principal, Hugh Stewart's professed aim was to gain it full university status. He himself did not live to see this aim realised, dying suddenly in September 1934 during his return from a visit to New Zealand. However during his time as Principal, Hugh Stewart was instrumental in setting the foundations for the College's eventual acquisition of a University charter in 1948. Following his death the University College's hostel for male students, Lenton Hall, was substantially enlarged and renamed in his honour as Hugh Stewart Hall.
Hugh Stewart was married three times, firstly to Alexandrina K. Johnston with whom he had his eldest son Michael. Alexandrina died in 1920. In 1927 he married Margaret Poulton who died the following year. In 1930 he married Margaret Massey with whom he had two children, Margaret Judith and John Hugh Hamon Massey.
After her husband's death Mrs Massey Stewart maintained close ties to the University College, afterwards the University of Nottingham, being appointed a life member of the Court of Governors in 1938 and being a frequent presence at University College functions. In 1937 she gave money for the endowment of a scholarship in memory of her late husband. The Hugh Stewart Scholarship was awarded bienially to male arts graduates. The presence of numerous newspaper cuttings concerning the University College and University in this collection dating from after Principal Stewart's death testify to Mrs Stewart's continued and lifelong interest in the University.