From 1955 through 1958, Bobby Cleary played hockey for Harvard and broke the school scoring record, set by his older brother, Billy. Bobby led the nation in scoring in both his junior and senior years, captained the team as a senior, and was twice named to the NCAA All-American team. In addition he played three years of varsity baseball, also captaining that team in his senior year, and played three seasons in the well-known Cape Cod Baseball League.
After leaving college, Cleary played for the 1960 gold medalists, went into the insurance business, and set up a casualty and property insurance company with his older brother. The Cleary brothers had missed the Olympic try-outs through business commitments and their late call-up to the roster was originally very unpopular with their teammates. Bobby Cleary became a life member of the Million Dollar Round Table and was one of the few agents to win the Flagship Award for top life insurance sales in multiple years. Cleary is a member of the US Hockey Hall of Fame, the Massachusetts Hockey Hall of Fame, and the Harvard Varsity Club Hall of Fame.