The Nationalist Chinese government recruited Yip to the post of captain of the police. After the Communist triumph in 1949, Yip left his two grown sons in Fatshan and fled to Hong Kong. His position as police captain would have meant almost certain death at the hands of the Communists had he remained. Thus at the age of 51, Yip Man was forced to start an entirely new life.

Yip Man started teaching at the Restaurant Union Hall. His classes had grown so large that he had to leave the Union Hall and opened his first commercial Wing Chun School on Lei Dat Street in Yaumatie District of Kowloon. As the years passed, Yip's reputation as an instructor grew and he was eventually able to afford better accommodations. In fact, by 1964 he was able to bring his two sons and their families out of mainland China. Three years later, due in part of the prosperity brought to him through Bruce Lee's Green Hornet fame, Yip made his final move to a large, well equipped gymnasium. Only after the name of Bruce Lee did the other students realize that the master was so great, and that the style was so great, because they saw that it could produce practitioners like Bruce. They had not realized the treasure they had in Yip Man and had taken him for granted.