Alan McCleery began competing at the junior national level in the late 1940s and had advanced to senior-level competition by the early 1950s. In 1956, he and Lou Lukanovich won the Canadian K-2 1000 Olympic trials but, as Luckanovich was not yet a Canadian citizen, the berth went to Robert Smith and Les Melia instead. When McCleery and Lukanovich won the trials again in 1960, citizenship was no longer an issue and they were sent to the Rome Games, where they were eliminated in the repêchage. McCleery retired from active competition shortly thereafter, but remained active in rowing into his 90s, including as a coach and trainer at the Cartierville Boating Club for over a decade. By career, he worked for Bell Canada.