|Like his older brother Bill, Bob Cleary played prep school hockey at Belmont Hill before going on to a stellar career at Harvard University. He topped the NCAA in scoring in both 1956-57 and 1957-58. Cleary served as team captain in 1957-58 and was selected as an All-American that season.
In 1959, Cleary played for the United States National Team at the World Championships and in 1960 he was a late addition to the U.S. Olympic team. Cleary teamed with his brother Bill and former Harvard teammate Bob McVey to form a high-scoring line that helped the Americans win a surprising gold medal in Squaw Valley, California.