At the age of 16, Yip Man was then accepted as a student of Leung Bik, the son of Yip Man's teacher's teacher. Yip Man had challenged Leung Bik unaware that he too was a Wing Chun practitioner. Leung Bik explained how his father, Dr. Leung Jan, had withheld key elements of the Wing Chun system from Chan Wan Shun. Chan had been over six feet tall, whereas Dr. Leung's two sons only stood at about five feet. In order to give his sons a slight technical edge, Dr. Leung did not teach Chan Wah Shun the proper interrupted footwork patterns. Further, he held back many techniques even from the three forms. Yip studied with Leung Bik for two and a half years.

Between 1937 and 1941, Yip served in the army during China's valiant effort to repel the Japanese invasion. He returned home to his family in Fatshan during the years of the occupation. Times were hard. His farm was in ruin and his wife was ill and subsequently died. The end of the war brought little improvement.