Cleary played as a fullback and won two best and fairest awards for South Melbourne, in 1942 and 1944. His reputation was marred somewhat by his involvement in what is referred to as the 1945 VFL Grand Final 'bloodbath'. For his part in the incident he was suspended for 8 matches. He left the club in 1948 and went on to become captain and coach of Port Melbourne. After a successful stint with Port he continued his coaching career at both Brunswick and Dandenong. He remained involved in the game even after retiring as a coach, becoming a panelist on a TV show called 'World of Sport'.