[1] In late 1942, Checkland enrolled at the Royal Military College, Sandhurst, then was commissioned as a lieutenant into the Manchester Regiment, before becoming a tank commander in the Governor General's Foot Guards of the Canadian Army.
[1] After the war, Checkland joined the Common Wealth Party and stood unsuccessfully in Sheffield Ecclesall at the 1945 general election.
He then returned to study for a master's degree at Birmingham, after which he took up an academic post in economic science at the University of Liverpool, where he also obtained a doctorate.
He quickly developed a strong reputation in a range of fields relating to economic history, and continued to write until his death in 1986.
[1] He is credited with "being instrumental" in the establishment in 1976 of the Faculty of Social Sciences at the University of Glasgow "strong in the fields of business, banking, and urban history".